JP5454764B2 - Method for producing biaryl compounds - Google Patents

Description

  The present invention relates to a method for producing a biaryl compound.

Many biaryl derivatives exist in nature, and are also useful as intermediates for the production of catalysts, pharmaceuticals, functional materials and the like. However, since biaryl compounds have many substitution modes, selective synthesis of substitution positions has been difficult. As methods for synthesizing existing substituted biaryl compounds, an electrophilic substitution reaction to an existing biaryl skeleton (see, for example, Non-Patent Document 1) or a cross-coupling reaction with a transition metal catalyst (see, for example, Non-Patent Document 2). ).
Jerry March, Advanced Organic Chemistry, 4th ed., Wiley, New York, 1992, Chapter 11, p501. Norio Miyaura, Akira Suzuki, Chem. Rev., 1995, 95, 2457-2483.

  However, there is a problem that the biaryl derivatives obtained by the techniques described in Non-Patent Documents 1 and 2 are limited.

  Then, in view of the said subject, this invention aims at providing the manufacturing method which obtains the biaryl compound which has various substitution modes efficiently and simply.

  As a result of intensive studies on the above problems, the present inventors have conducted a tandem ring-closing enyne metathesis / ring-closing olefin metathesis reaction of an ene-in compound having various substituents that can be easily synthesized in the presence of a ruthenium catalyst. It has been found that various biaryl compounds can be produced.

That is, in the first aspect of the present invention, an enyne represented by the following general formula (1) is reacted in the presence of a ruthenium or molybdenum catalyst to generate a cyclic compound represented by the following general formula (2). Furthermore, it is a method for producing a biaryl compound represented by the following general formula (3) by causing thermal decomposition or reaction in the presence of an acid or a base.

In the general formula (1), R ^{1 to} R ¹⁶ are a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group that may have a substituent, or a C _{1 to} C ₂₀ that may have a substituent. alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, which may have a substituent silyl group, substituted which may be an alkylthio group (-SY ^1, in the formula, Y ¹ is a good C ₁ -C ₂₀ alkyl group which may have a substituent.), which may have a substituent arylthio group ( -SY ^2, in the formula, Y ² is a good C ₆ -C ₂₀ aryl group which may have a substituent.), which may have a substituent alkylsulfonyl group (-SO ₂ Y ^3, In the formula, Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group.), An optionally substituted arylsulfonyl group (—SO ₂ Y ⁴ , wherein Y ⁴ has a substituent Can have represents an C ₆ -C ₂₀ aryl group.), A hydroxyl group or a halogen atom. R ^{1 to} R ¹⁶ are independent of each other and may be the same or different. R ¹ and R ² , R ³ and R ⁴ , R ⁴ and R ⁶ , R ⁶ and R ⁷ , R ⁷ and R ⁸ , R ⁹ and R ¹⁰ , R ¹⁰ and R ¹² , R ¹² and R ¹³ , R ¹³ and R ¹⁴ , and R ¹⁵ and R ¹⁶ may be bridged with each other to form a C _{4 to} C ₁₀ saturated or unsaturated ring, and in the case of the ring, an oxygen atom, a sulfur atom , silicon atom, tin atom, germanium atom or -N (B) - group (. where B is a hydrogen atom or a C ₁ -C ₁₀ hydrocarbon group) represented by may be interrupted by, and, It may have a substituent.

In the general formula (2), R ^{3 to} R ¹⁴ are each a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group that may have a substituent, or a C _{1 to} C ₂₀ that may have a substituent. Alkoxy group, C ₆ -C ₂₀ aryloxy group optionally having substituent, amino group optionally having substituent, silyl group optionally having substituent, having substituent which may be an alkylthio group (-SY ^1, in the formula, Y ¹ is a good C ₁ -C ₂₀ alkyl group which may have a substituent.), which may have a substituent arylthio group ( -SY ^2, in the formula, Y ² is a good C ₆ -C ₂₀ aryl group which may have a substituent.), which may have a substituent alkylsulfonyl group (-SO ₂ Y ^3, In the formula, Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group.), An optionally substituted arylsulfonyl group (—SO ₂ Y ⁴ , wherein Y ⁴ has a substituent Can have represents an C ₆ -C ₂₀ aryl group.), A hydroxyl group or a halogen atom. R ^{3 to} R ¹⁴ are independent of each other and may be the same or different. Also, R ³ and R ^4, R ⁴ and R ^6, R ⁶ and R ^7, R ⁷ and R ^8, R ⁹ and R ^10, R ¹⁰ and R ^12, R ¹² and R ^13, and R ¹³ and R ¹⁴ May be bridged with each other to form a C _{4 to} C ₁₀ saturated ring or unsaturated ring, and in the case of the ring, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom, or —N ( B) -. group (wherein B represented by may be interrupted by a hydrogen atom or a C ₁ -C ₁₀ hydrocarbon group), and may have a substituent.

In the general formula ^{(3), R 3, R} 4, R 6 ~R 10, R 12 ~R 14 is a hydrogen atom, which may have a substituent C ₁ -C ₂₀ hydrocarbon group, a substituent which may have a C ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, substituted An optionally substituted silyl group, an optionally substituted alkylthio group (-SY ¹ , wherein Y ¹ represents an optionally substituted C ₁ -C ₂₀ alkyl group), also an optionally substituted arylthio group (-SY ^2, in the formula, Y ² is a good C ₆ -C ₂₀ aryl group which may have a substituent.), have a substituent which may alkylsulfonyl group (-SO ₂ Y ^3, in the formula, Y ³ represents a good C ₁ -C ₂₀ alkyl group which may have a substituent.), an arylsulfonyl optionally having substituent group (-SO ₂ Y ^4, wherein , Y ⁴ represents a good C ₆ -C ₂₀ aryl group which may have a substituent.), A hydroxyl group or a halogen atom. R ^{3 to} R ¹⁴ are independent of each other and may be the same or different. Also, R ³ and R ^4, R ⁴ and R ^6, R ⁶ and R ^7, R ⁷ and R ^8, R ⁹ and R ^10, R ¹⁰ and R ^12, R ¹² and R ^13, and R ¹³ and R ¹⁴ May be bridged with each other to form a C _{4 to} C ₁₀ saturated ring or unsaturated ring, and in the case of the ring, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom, or —N ( B) -. group (wherein B represented by may be interrupted by a hydrogen atom or a C ₁ -C ₁₀ hydrocarbon group), and may have a substituent.

The second embodiment of the present invention is a method for producing a biaryl compound represented by the general formula (5) by reacting a dienein represented by the following general formula (4) in the presence of a ruthenium or molybdenum catalyst. It is.

In the above general formula (4), R ^{1 to} R ⁴ , R ^{7 to} R ¹⁰ , R ^{13 to} R ¹⁶ are hydrogen atoms and optionally substituted C _{1 to} C ₂₀ hydrocarbon groups, substituted Yes it may have a group C ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, a substituent An optionally substituted silyl group and an optionally substituted alkylthio group (—SY ¹ , wherein Y ¹ represents an optionally substituted C _{1 to} C ₂₀ alkyl group). , An optionally substituted arylthio group (—SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), has a substituent An optionally substituted alkylsulfonyl group (—SO ₂ Y ³ , wherein Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group), an optionally substituted aryl Sulfonyl group (-SO ₂ Y ⁴ In the formula, Y ⁴ represents an optionally substituted C ₆ -C ₂₀ aryl group.), A hydroxyl group, or a halogen atom. R ^{1 to} R ⁴ , R ^{7 to} R ¹⁰ , and R ^{13 to} R ¹⁶ are independent of each other and may be the same or different. R ¹ and R ² , R ³ and R ⁴ , R ⁷ and R ⁸ , R ⁹ and R ¹⁰ , R ¹³ and R ¹⁴ , R ¹⁵ and R ¹⁶ are cross-linked with each other to be saturated with C _{4 to} C _10. A ring or an unsaturated ring may be formed, and in the case of the ring, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom, or a group represented by the formula —N (B) — (wherein B is A hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group.) And may have a substituent. X is an oxygen atom, a sulfur atom or a nitrogen atom which may have a substituent.

Further, in the above general formula ^{(5), R 3, R} 4, R 7 ~R 10, R 13, R 14, are hydrogen atoms, which may have a substituent C ₁ -C ₂₀ hydrocarbon group, which may have a substituent C ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, a substituent A silyl group which may have, and an alkylthio group which may have a substituent (—SY ¹ , wherein Y ¹ represents a C _{1 to} C ₂₀ alkyl group which may have a substituent. ), An optionally substituted arylthio group (—SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), has a substituent An optionally substituted alkylsulfonyl group (—SO ₂ Y ³ , wherein Y ³ represents a C _{1 to} C ₂₀ alkyl group which may have a substituent), and may have a substituent. Arylsulfonyl group (—SO ₂ Y ⁴ , wherein Y ⁴ represents an optionally substituted C ₆ -C ₂₀ aryl group), a hydroxyl group, or a halogen atom. R ³ , R ⁴ , R ^{7 to} R ¹⁰ , R ¹³ , and R ¹⁴ are independent of each other and may be the same or different. R ³ and R ⁴ , R ⁷ and R ⁸ , R ⁹ and R ¹⁰ , R ¹³ and R ¹⁴ may be bridged with each other to form a C _{4 to} C ₁₀ saturated or unsaturated ring, In the case of the ring, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom or a group represented by the formula —N (B) — (wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) May be interrupted and may have a substituent. X is an oxygen atom, a sulfur atom or a nitrogen atom which may have a substituent.

The third aspect of the present invention is to react an enyne represented by the following general formula (6) in the presence of a ruthenium or molybdenum catalyst to generate a cyclic compound represented by the following general formula (7). And a method for producing a biaryl compound represented by the following general formula (8) by further thermal decomposition or reaction in the presence of an acid or a base.

In the general formula (6), R ^{1 to} R ¹⁶ are a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group that may have a substituent, or a C ₁ to C that may have a substituent. C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, which may have a substituent silyl group, a substituent have alkylthio group (-SY ^1, shown in the formula, Y ¹ is an optionally C ₁ -C ₂₀ alkyl group which may have a substituent.) may arylthio optionally having substituent A group (—SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), an optionally substituted alkylsulfonyl group (—SO ₂ Y ³ , wherein Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group.), An optionally substituted arylsulfonyl group (—SO ₂ Y ⁴ , , Y ⁴ is a substituted group Have shown even better C ₆ -C ₂₀ aryl group optionally.), A hydroxyl group, or a halogen atom. R ^{1 to} R ¹⁶ are independent of each other and may be the same or different. R ¹ and R ² , R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁷ , R ⁷ and R ⁸ , R ⁹ and R ¹¹ , R ¹¹ and R ¹² , R ¹² and R ¹³ , R ¹³ and R ¹⁴ , R ¹⁵ and R ¹⁶ may be bridged with each other to form a C _{4 to} C ₁₀ saturated or unsaturated ring, and in the case of the ring, an oxygen atom, a sulfur atom, silicon atom, tin atom, germanium atom or the formula -N (B) - group (. wherein, B is a hydrogen atom or a C ₁ -C ₁₀ hydrocarbon group) represented by may be interrupted by, and, It may have a substituent.

In the general formula (7), R ^{3 to} R ¹⁴ are a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group that may have a substituent, or a C _{1 to} C that may have a substituent. ₂₀ alkoxy group, optionally substituted C ₆ -C ₂₀ aryloxy group, optionally substituted amino group, optionally substituted silyl group, substituted An optionally substituted alkylthio group (—SY ¹ , wherein Y ¹ represents an optionally substituted C ₁ -C ₂₀ alkyl group), an optionally substituted arylthio group (—SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), an optionally substituted alkylsulfonyl group (—SO ₂ Y ³ In the formula, Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group.), An optionally substituted arylsulfonyl group (—SO ₂ Y ⁴ , Y ⁴ is a substituent And shows also good C ₆ -C ₂₀ aryl group optionally.), A hydroxyl group, or a halogen atom. R ^{3 to} R ¹⁴ are independent of each other and may be the same or different. R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁷ , R ⁷ and R ⁸ , R ⁹ and R ¹¹ , R ¹¹ and R ¹² , R ¹² and R ¹³ , R ¹³ and R ¹⁴ are , respectively, in the case of C ₄ -C ₁₀ may form a saturated or unsaturated ring, wherein said ring crosslinked to each other, an oxygen atom, a sulfur atom, a silicon atom, tin atom, germanium atom or the formula -N ( B) — may be interrupted by a group represented by the formula (wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) and may have a substituent.

In the above general formula (8), R ^{3 to} R ⁵ , R ^{7 to} R ⁹ , and R ^{11 to} R ¹⁴ are a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group that may have a substituent, and a substituent. Yes it may have a group C ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, a substituent An optionally substituted silyl group and an optionally substituted alkylthio group (—SY ¹ , wherein Y ¹ represents an optionally substituted C _{1 to} C ₂₀ alkyl group). , An optionally substituted arylthio group (—SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), has a substituent An optionally substituted alkylsulfonyl group (—SO ₂ Y ³ , wherein Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group), an optionally substituted aryl a sulfonyl group (-SO ₂ Y ⁴ In the formula, Y ⁴ is a good C ₆ -C ₂₀ aryl group which may have a substituent.), A hydroxyl group, or a halogen atom. R ^{3 to} R ⁵ , R ^{7 to} R ⁹ , and R ^{11 to} R ¹⁴ are independent of each other and may be the same or different. R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁷ , R ⁷ and R ⁸ , R ⁹ and R ¹¹ , R ¹¹ and R ¹² , R ¹² and R ¹³ , R ¹³ and R ¹⁴ are , respectively, in the case of C ₄ -C ₁₀ may form a saturated or unsaturated ring, wherein said ring crosslinked to each other, an oxygen atom, a sulfur atom, a silicon atom, tin atom, germanium atom or the formula -N ( B) — may be interrupted by a group represented by the formula (wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) and may have a substituent.

According to a fourth aspect of the present invention, there is provided a biaryl compound represented by the general formula (10), wherein the diene in represented by the following general formula (9) is reacted in the presence of a ruthenium or molybdenum catalyst. It is a manufacturing method.

In the above general formula (9), R ^{1 to} R ⁵ , R ⁸ , R ⁹ and R ^{12 to} R ¹⁶ are hydrogen atoms, C _{1 to} C ₂₀ hydrocarbon groups which may have a substituent, and substituents. Yes it may have a group C ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, a substituent An optionally substituted silyl group and an optionally substituted alkylthio group (—SY ¹ , wherein Y ¹ represents an optionally substituted C _{1 to} C ₂₀ alkyl group). , An optionally substituted arylthio group (—SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), has a substituent An optionally substituted alkylsulfonyl group (—SO ₂ Y ³ , wherein Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group), an optionally substituted aryl a sulfonyl group (-SO ₂ Y ⁴ In the formula, Y ⁴ is a good C ₆ -C ₂₀ aryl group which may have a substituent.), A hydroxyl group, or a halogen atom. R ^{1 to} R ⁵ , R ⁸ , R ⁹ and R ^{12 to} R ¹⁶ are independent of each other and may be the same or different. R ¹ and R ² , R ³ and R ⁴ , R ⁴ and R ⁵ , R ¹² and R ¹³ , R ¹³ and R ¹⁴ , R ¹⁵ and R ¹⁶ are cross-linked with each other to be saturated with C _{4 to} C _10. A ring or an unsaturated ring may be formed, and in the case of the ring, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom, or a group represented by the formula —N (B) — (wherein B is A hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group.) And may have a substituent. X is an oxygen atom, a sulfur atom, or a nitrogen atom that may have a substituent.

In the general formula (10), R ^{3 to} R ⁵ , R ⁸ , R ⁹ , and R ^{12 to} R ¹⁴ are a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group that may have a substituent, which may have a substituent C ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, a substituent A silyl group which may have, and an alkylthio group which may have a substituent (—SY ¹ , wherein Y ¹ represents a C _{1 to} C ₂₀ alkyl group which may have a substituent. ), An optionally substituted arylthio group (—SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), has a substituent An optionally substituted alkylsulfonyl group (—SO ₂ Y ³ , wherein Y ³ represents a C _{1 to} C ₂₀ alkyl group which may have a substituent), and may have a substituent. Arylsulfonyl group (—SO ₂ Y ⁴ , wherein Y ⁴ represents a C ₆ -C ₂₀ aryl group which may have a substituent), a hydroxyl group, or a halogen atom. R ^{3 to} R ⁵ , R ⁸ , R ⁹ and R ^{12 to} R ¹⁴ are independent of each other and may be the same or different. R ³ and R ⁴ , R ⁴ and R ⁵ , R ¹² and R ¹³ , R ¹³ and R ¹⁴ may be bridged with each other to form a C _{4 to} C ₁₀ saturated or unsaturated ring, In the case of the ring, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom or a group represented by the formula —N (B) — (wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) May be interrupted and may have a substituent. X is an oxygen atom, a sulfur atom, or a nitrogen atom that may have a substituent.

The fifth aspect of the present invention is to react the enyne represented by the following general formula (11) in the presence of a ruthenium or molybdenum catalyst to generate a cyclic compound represented by the general formula (12). This is a method for producing a biaryl compound represented by the following general formula (13), in which this is thermally decomposed or reacted in the presence of an acid or a base.

In the general formula (11), R ^{1 to} R ¹⁶ are a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group that may have a substituent, or a C _{1 to} C that may have a substituent. ₂₀ alkoxy group, optionally substituted C ₆ -C ₂₀ aryloxy group, optionally substituted amino group, optionally substituted silyl group, substituted An optionally substituted alkylthio group (—SY ¹ , wherein Y ¹ represents an optionally substituted C ₁ -C ₂₀ alkyl group), an optionally substituted arylthio group (—SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), an optionally substituted alkylsulfonyl group (—SO ₂ Y ³ In the formula, Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group.), An optionally substituted arylsulfonyl group (—SO ₂ Y ⁴ , Y ⁴ is a substituted group Have shown even better C ₆ -C ₂₀ aryl group optionally.), A hydroxyl group, or a halogen atom. R ^{1 to} R ¹⁶ are independent of each other and may be the same or different. R ¹ and R ² , R ³ and R ⁵ , R ⁵ and R ⁶ , R ⁶ and R ⁷ , R ⁷ and R ⁸ , R ⁹ and R ¹⁰ , R ¹⁰ and R ¹¹ , R ¹¹ and R ¹³ , R ¹³ and R ¹⁴ , R ¹⁵ and R ¹⁶ may be bridged with each other to form a C _{4 to} C ₁₀ saturated or unsaturated ring, and in the case of the ring, an oxygen atom, a sulfur atom, silicon atom, tin atom, germanium atom or the formula -N (B) - group (. wherein, B is a hydrogen atom or a C ₁ -C ₁₀ hydrocarbon group) represented by may be interrupted by, and, It may have a substituent.

In the general formula (12), R ^{3 to} R ¹⁴ are each a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group which may have a substituent, or a C ₁ to which may have a substituent. C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, which may have a substituent silyl group, a substituent have alkylthio group (-SY ^1, shown in the formula, Y ¹ is an optionally C ₁ -C ₂₀ alkyl group which may have a substituent.) may arylthio optionally having substituent A group (—SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), an optionally substituted alkylsulfonyl group (—SO ₂ Y ³ , wherein Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group.), An optionally substituted arylsulfonyl group (—SO ₂ Y ⁴ , , Y ⁴ is a substituted Even when the have shown a good C ₆ -C ₂₀ aryl group.), A hydroxyl group, or a halogen atom. R ^{3 to} R ¹⁴ are independent of each other and may be the same or different. R ³ and R ⁵ , R ⁵ and R ⁶ , R ⁶ and R ⁷ , R ⁷ and R ⁸ , R ⁹ and R ¹⁰ , R ¹⁰ and R ¹¹ , R ¹¹ and R ¹³ , R ¹³ and R ¹⁴ are , respectively, in the case of C ₄ -C ₁₀ may form a saturated or unsaturated ring, wherein said ring crosslinked to each other, an oxygen atom, a sulfur atom, a silicon atom, tin atom, germanium atom or the formula -N ( B) — may be interrupted by a group represented by the formula (wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) and may have a substituent.

In the general formula (13), R ³ , R ^{5 to} R ¹¹ , R ¹³ , and R ¹⁴ have a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group that may have a substituent, and a substituent. and C ₁ optionally -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, substituted An optionally substituted silyl group, an optionally substituted alkylthio group (—SY ¹ , wherein Y ¹ represents an optionally substituted C ₁ -C ₂₀ alkyl group), a substituent. An arylthio group (-SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), may have a substituent An alkylsulfonyl group (—SO ₂ Y ³ , wherein Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group), an optionally substituted arylsulfonyl group ( -SO ₂ Y ^4, In, Y ⁴ represents a good C ₆ -C ₂₀ aryl group which may have a substituent.), A hydroxyl group, or a halogen atom. R ³ , R ^{5 to} R ¹¹ , R ¹³ and R ¹⁴ are independent of each other and may be the same or different. R ³ and R ⁵ , R ⁵ and R ⁶ , R ⁶ and R ⁷ , R ⁷ and R ⁸ , R ⁹ and R ¹⁰ , R ¹⁰ and R ¹¹ , R ¹¹ and R ¹³ , R ¹³ and R ¹⁴ are , respectively, in the case of C ₄ -C ₁₀ may form a saturated or unsaturated ring, wherein said ring crosslinked to each other, an oxygen atom, a sulfur atom, a silicon atom, tin atom, germanium atom or the formula -N ( B) — may be interrupted by a group represented by the formula (wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) and may have a substituent.

The sixth aspect of the present invention is a method for producing a biaryl compound represented by the following general formula (15) by reacting a dienein represented by the following general formula (14) in the presence of a ruthenium or molybdenum catalyst. It is.

In the general formula (14), R ^{1 to} R ³ , R ^{6 to} R ¹¹ , and R ^{14 to} R ¹⁶ are a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group which may have a substituent, and a substituent. which may have a C ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, substituted An optionally substituted silyl group, an optionally substituted alkylthio group (-SY ¹ , wherein Y ¹ represents an optionally substituted C ₁ -C ₂₀ alkyl group), also an optionally substituted arylthio group (-SY ^2, in the formula, Y ² is a good C ₆ -C ₂₀ aryl group which may have a substituent.), have a substituent which may alkylsulfonyl group (-SO ₂ Y ^3, in the formula, Y ³ represents a good C ₁ -C ₂₀ alkyl group which may have a substituent.), an arylsulfonyl optionally having substituent group (-SO ₂ Y ⁴ In the formula, Y ⁴ is a good C ₆ -C ₂₀ aryl group which may have a substituent.), A hydroxyl group or a halogen atom. R ^{1 to} R ³ , R ^{6 to} R ¹¹ , and R ^{14 to} R ¹⁶ are independent of each other and may be the same or different. R ¹ and R ² , R ⁶ and R ⁷ , R ⁷ and R ⁸ , R ⁹ and R ¹⁰ , R ¹⁰ and R ¹¹ , R ¹⁵ and R ¹⁶ are cross-linked with each other to be saturated with C _{4 to} C _10. A ring or an unsaturated ring may be formed, and in the case of the ring, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom, or a group represented by the formula —N (B) — (wherein B is A hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group.) And may have a substituent. X is an oxygen atom, a sulfur atom or a nitrogen atom which may have a substituent.

In the general formula (15), R ³ , R ^{6 to} R ¹¹ and R ¹⁴ may have a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group which may have a substituent, or a substituent. good C ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, a silyl group, which may have a substituent , which may have a substituent alkylthio group (-SY ^1, wherein, Y ¹ is. showing a good C ₁ -C ₂₀ alkyl group which may have a substituent), have a substituent An optionally substituted arylthio group (—SY ² , wherein Y ² represents an optionally substituted C _{6 to} C ₂₀ aryl group), an optionally substituted alkylsulfonyl group ( —SO ₂ Y ³ , wherein Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group), and optionally substituted arylsulfonyl group (—SO ₂ Y ^4, in the formula, Y ⁴ May have a substituent represents an C ₆ -C ₂₀ aryl group.), A hydroxyl group or a halogen atom. R ³ , R ^{6 to} R ¹¹ and R ¹⁴ are independent of each other and may be the same or different. R ⁶ and R ⁷ , R ⁷ and R ⁸ , R ⁹ and R ¹⁰ , R ¹⁰ and R ¹¹ may be bridged with each other to form a C _{4 to} C ₁₀ saturated or unsaturated ring, In the case of the ring, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom or a group represented by the formula —N (B) — (wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) May be interrupted and may have a substituent. X is an oxygen atom, a sulfur atom or a nitrogen atom which may have a substituent.

The seventh aspect of the present invention is to react a enein represented by the following general formula (16) in the presence of a ruthenium or molybdenum catalyst to generate a cyclic compound represented by the following general formula (17). Furthermore, it is a method for producing a biaryl compound represented by the following general formula (18) by causing thermal decomposition or reaction in the presence of an acid or a base.

In the general formula (16), R ^{1 to} R ¹⁶ are a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group that may have a substituent, or a C _{1 to} C that may have a substituent. ₂₀ alkoxy group, optionally substituted C ₆ -C ₂₀ aryloxy group, optionally substituted amino group, optionally substituted silyl group, substituted An optionally substituted alkylthio group (—SY ¹ , wherein Y ¹ represents an optionally substituted C ₁ -C ₂₀ alkyl group), an optionally substituted arylthio group (—SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), an optionally substituted alkylsulfonyl group (—SO ₂ Y ³ In the formula, Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group.), An optionally substituted arylsulfonyl group (—SO ₂ Y ⁴ , Y ⁴ is a substituted group Have shown a good C ₆ -C ₂₀ aryl group.), There Oh a hydroxyl group or a halogen atom. R ^{1 to} R ¹⁶ are independent of each other and may be the same or different. R ¹ and R ² , R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ⁶ and R ⁸ , R ¹⁰ and R ¹¹ , R ¹¹ and R ¹² , R ¹² and R ¹³ , R ¹³ and R ¹⁴ , R ¹⁵ and R ¹⁶ may be bridged with each other to form a C _{4 to} C ₁₀ saturated or unsaturated ring, and in the case of the ring, an oxygen atom, a sulfur atom, a silicon atom , Tin atom, germanium atom or a group represented by the formula —N (B) — (wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group), and substituted It may have a group. )

In the general formula (17), R ^{3 to} R ¹⁴ are each a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group that may have a substituent, or a C _{1 to} C ₂₀ that may have a substituent. alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, which may have a substituent silyl group, substituted which may be an alkylthio group (-SY ^1, in the formula, Y ¹ is a good C ₁ -C ₂₀ alkyl group which may have a substituent.), which may have a substituent arylthio group ( -SY ^2, in the formula, Y ² is a good C ₆ -C ₂₀ aryl group which may have a substituent.), which may have a substituent alkylsulfonyl group (-SO ₂ Y ^3, In the formula, Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group.), An optionally substituted arylsulfonyl group (—SO ₂ Y ⁴ , wherein Y ⁴ have a substituent Even though showing a good C ₆ -C ₂₀ aryl group.), There Oh a hydroxyl group or a halogen atom. R ^{3 to} R ¹³ are independent of each other and may be the same or different. R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ⁶ and R ⁸ , R ¹⁰ and R ¹¹ , R ¹¹ and R ¹² , R ¹² and R ¹³ , R ¹³ and R ¹⁴ are Each may be bridged with each other to form a C _{4 to} C ₁₀ saturated or unsaturated ring, in the case of said rings, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom or a formula —N (B ) — (Wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) and may have a substituent.

In the general formula (18), R ^{3 to} R ⁶ , R ⁸ and R ^{10 to} R ¹⁴ have a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group which may have a substituent, and a substituent. which may be C ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, which may have a substituent a silyl group which may have a substituent alkylthio group (-SY ^1, in the formula, Y ¹ is a good C ₁ -C ₂₀ alkyl group which may have a substituent.), a substituent have good arylthio group (-SY ^2, in the formula, Y ² is a good C ₆ -C ₂₀ aryl group which may have a substituent.), an alkyl which may have a substituent A sulfonyl group (—SO ₂ Y ³ , wherein Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group), an optionally substituted arylsulfonyl group (— SO ₂ Y ⁴ , where Y ⁴ represents an optionally substituted C ₆ -C ₂₀ aryl group.), A hydroxyl group or a halogen atom. R ^{3 to} R ⁶ , R ⁸ and R ^{10 to} R ¹⁴ are independent of each other and may be the same or different. R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ⁶ and R ⁸ , R ¹⁰ and R ¹¹ , R ¹¹ and R ¹² , R ¹² and R ¹³ , R ¹³ and R ¹⁴ are Each may be bridged with each other to form a C _{4 to} C ₁₀ saturated or unsaturated ring, in the case of said rings, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom or a formula —N (B ) — (Wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) and may have a substituent.

The eighth aspect of the present invention is a method for producing a biaryl compound represented by the following general formula (20) by reacting the dienein represented by the general formula (19) in the presence of a ruthenium or molybdenum catalyst. is there.

In the general formula ^{(19), R 1 ~R 6} , R 11 ~R 16 is hydrogen atom, which may have a substituent C ₁ -C ₂₀ hydrocarbon group, which may have a substituent good C ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, a silyl group, which may have a substituent , which may have a substituent alkylthio group (-SY ^1, wherein, Y ¹ is. showing a good C ₁ -C ₂₀ alkyl group which may have a substituent), have a substituent An optionally substituted arylthio group (—SY ² , wherein Y ² represents an optionally substituted C _{6 to} C ₂₀ aryl group), an optionally substituted alkylsulfonyl group ( —SO ₂ Y ³ , wherein Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group), and optionally substituted arylsulfonyl group (—SO ₂ Y ^4: in the formula, Y ⁴ Have a substituent represents an C ₆ -C ₂₀ aryl group.), A hydroxyl group or a halogen atom. R ^{1 to} R ⁶ and R ^{11 to} R ¹⁶ are independent of each other and may be the same or different. R ¹ and R ² , R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ¹¹ and R ¹² , R ¹² and R ¹³ , R ¹³ and R ¹⁴ , R ¹⁵ and R ¹⁶ are Each may be bridged with each other to form a C _{4 to} C ₁₀ saturated or unsaturated ring, in the case of said rings, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom or a formula —N (B ) — (Wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) and may have a substituent. X is an oxygen atom; a sulfur atom; or a nitrogen atom that may have a substituent.

In the general formula ^{(20), R 3 ~R 6} , R 11 ~R 14 is a hydrogen atom, which may have a substituent C ₁ -C ₂₀ hydrocarbon group, which may have a substituent good C ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, a silyl group, which may have a substituent , which may have a substituent alkylthio group (-SY ^1, wherein, Y ¹ is. showing a good C ₁ -C ₂₀ alkyl group which may have a substituent), have a substituent An optionally substituted arylthio group (—SY ² , wherein Y ² represents an optionally substituted C _{6 to} C ₂₀ aryl group), an optionally substituted alkylsulfonyl group ( —SO ₂ Y ³ , wherein Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group), and optionally substituted arylsulfonyl group (—SO ₂ Y ^4: in the formula, Y ⁴ Have a substituent represents an C ₆ -C ₂₀ aryl group.), A hydroxyl group or a halogen atom. R ^{3 to} R ⁶ and R ^{11 to} R ¹⁴ are independent of each other and may be the same or different. R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ¹¹ and R ¹² , R ¹² and R ¹³ , R ¹³ and R ¹⁴ are each cross-linked and C _{4 to} C ₁₀ saturated. A ring or an unsaturated ring may be formed, and in the case of the ring, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom, or a group represented by the formula —N (B) — (wherein B is A hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group.) And may have a substituent. X is an oxygen atom; a sulfur atom; or a nitrogen atom that may have a substituent.

In the ninth aspect of the present invention, an enyne represented by the following general formula (21) is reacted in the presence of a ruthenium or molybdenum catalyst to generate a cyclic compound represented by the following general formula (22), Furthermore, it is a method for producing a biaryl compound represented by the following general formula (23) by heat decomposition or reaction in the presence of an acid or a base.

In the general formula (21), R ¹ ~R ¹⁶ is hydrogen atom, which may have a substituent C ₁ -C ₂₀ hydrocarbon group which may have a substituent C ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, which may have a substituent silyl group, substituted which may be an alkylthio group (-SY ^1, in the formula, Y ¹ is a good C ₁ -C ₂₀ alkyl group which may have a substituent.), which may have a substituent arylthio group ( -SY ^2, in the formula, Y ² is a good C ₆ -C ₂₀ aryl group which may have a substituent.), which may have a substituent alkylsulfonyl group (-SO ₂ Y ^3, In the formula, Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group.), An optionally substituted arylsulfonyl group (—SO ₂ Y ⁴ , wherein Y ⁴ have a substituent Even though showing a good C ₆ -C ₂₀ aryl group.), A hydroxyl group or a halogen atom. R ^{1 to} R ¹⁶ are independent of each other and may be the same or different. R ¹ and R ² , R ³ and R ⁵ , R ⁵ and R ⁶ , R ⁶ and R ⁷ , R ⁷ and R ⁸ , R ⁹ and R ¹⁰ , R ¹⁰ and R ¹¹ , R ¹¹ and R ¹³ , R ¹³ and R ¹⁴ , R ¹⁵ and R ¹⁶ may be bridged with each other to form a C _{4 to} C ₁₀ saturated or unsaturated ring, and in the case of the ring, an oxygen atom, a sulfur atom, silicon atom, tin atom, germanium atom or the formula -N (B) - group (. wherein, B is a hydrogen atom or a C ₁ -C ₁₀ hydrocarbon group) represented by may be interrupted by, and, It may have a substituent.

In the general formula (22), R ^{3 to} R ¹⁴ are a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group that may have a substituent, or a C _{1 to} C ₂₀ that may have a substituent. alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, which may have a substituent silyl group, substituted which may be an alkylthio group (-SY ^1, in the formula, Y ¹ is a good C ₁ -C ₂₀ alkyl group which may have a substituent.), which may have a substituent arylthio group ( -SY ^2, in the formula, Y ² is a good C ₆ -C ₂₀ aryl group which may have a substituent.), which may have a substituent alkylsulfonyl group (-SO ₂ Y ^3, In the formula, Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group.), An optionally substituted arylsulfonyl group (—SO ₂ Y ⁴ , wherein Y ⁴ have a substituent Even though showing a good C ₆ -C ₂₀ aryl group.), A hydroxyl group or a halogen atom. R ^{3 to} R ¹⁴ are independent of each other and may be the same or different. R ³ and R ⁵ , R ⁵ and R ⁶ , R ⁶ and R ⁷ , R ⁷ and R ⁸ , R ⁹ and R ¹⁰ , R ¹⁰ and R ¹¹ , R ¹¹ and R ¹³ , R ¹³ and R ¹⁴ are , respectively, in the case of C ₄ -C ₁₀ may form a saturated or unsaturated ring, wherein said ring crosslinked to each other, an oxygen atom, a sulfur atom, a silicon atom, tin atom, germanium atom or the formula -N ( B) — may be interrupted by a group represented by the formula (wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) and may have a substituent.

In the general formula ^{(23), R 3, R} 5 ~R 11, R 13, R 14 is a hydrogen atom, which may have a substituent C ₁ -C ₂₀ hydrocarbon group, optionally having a substituent which may be C ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group which may have a substituent amino group, which may have a substituent a silyl group which may have a substituent alkylthio group (-SY ^1, in the formula, Y ¹ is a good C ₁ -C ₂₀ alkyl group which may have a substituent.), have a substituent An optionally substituted arylthio group (—SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), an optionally substituted alkylsulfonyl A group (—SO ₂ Y ³ , wherein Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group), an optionally substituted arylsulfonyl group (—SO 2 ₂ Y ⁴ , where Y ⁴ represents an optionally substituted C ₆ -C ₂₀ aryl group), a hydroxyl group or a halogen atom. R ³ , R ^{5 to} R ¹¹ , R ¹³ and R ¹⁴ are independent of each other and may be the same or different. R ³ and R ⁵ , R ⁵ and R ⁶ , R ⁶ and R ⁷ , R ⁷ and R ⁸ , R ⁹ and R ¹⁰ , R ¹⁰ and R ¹¹ , R ¹¹ and R ¹³ , R ¹³ and R ¹⁴ are , respectively, in the case of C ₄ -C ₁₀ may form a saturated or unsaturated ring, wherein said ring crosslinked to each other, an oxygen atom, a sulfur atom, a silicon atom, tin atom, germanium atom or the formula -N ( B) — may be interrupted by a group represented by the formula (wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) and may have a substituent.

The tenth aspect of the present invention is a method for producing a biaryl compound represented by the following general formula (25) by reacting a dienein represented by the following general formula (24) in the presence of a ruthenium or molybdenum catalyst. is there.

In the general formula (24), R ^{1 to} R ³ , R ^{6 to} R ¹¹ , and R ^{14 to} R ¹⁶ are a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group which may have a substituent, and a substituent. which may have a C ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, substituted An optionally substituted silyl group, an optionally substituted alkylthio group (-SY ¹ , wherein Y ¹ represents an optionally substituted C ₁ -C ₂₀ alkyl group), also an optionally substituted arylthio group (-SY ^2, in the formula, Y ² is a good C ₆ -C ₂₀ aryl group which may have a substituent.), have a substituent which may alkylsulfonyl group (-SO ₂ Y ^3, in the formula, Y ³ represents a good C ₁ -C ₂₀ alkyl group which may have a substituent.), an arylsulfonyl optionally having substituent group (-SO ₂ Y ⁴ In the formula, Y ⁴ is a good C ₆ -C ₂₀ aryl group which may have a substituent.), A hydroxyl group or a halogen atom. R ^{1 to} R ³ , R ^{6 to} R ¹¹ , and R ^{14 to} R ¹⁶ are independent of each other and may be the same or different. Also, R ¹ and R ² , R ⁶ and R ⁷ , R ⁷ and R ⁸ , R ⁹ and R ¹⁰ , R ¹⁰ and R ¹¹ , R ¹⁵ and R ¹⁶ are cross-linked with each other to form C _{4 to} C _10. A saturated ring or an unsaturated ring may be formed. In the case of the ring, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom, or a group represented by the formula —N (B) — (wherein B Is a hydrogen atom or a C ₁ -C ₁₀ hydrocarbon group.) And may have a substituent. X is an oxygen atom, a sulfur atom or a nitrogen atom which may have a substituent.

In the above general formula (25), R ³ , R ^{6 to} R ¹¹ and R ¹⁴ may have a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group which may have a substituent, or a substituent. good C ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, a silyl group, which may have a substituent , which may have a substituent alkylthio group (-SY ^1, wherein, Y ¹ is. showing a good C ₁ -C ₂₀ alkyl group which may have a substituent), have a substituent An optionally substituted arylthio group (—SY ² , wherein Y ² represents an optionally substituted C _{6 to} C ₂₀ aryl group), an optionally substituted alkylsulfonyl group ( —SO ₂ Y ³ , wherein Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group), and optionally substituted arylsulfonyl group (—SO ₂ Y ^4, in the formula, Y ⁴ May have a substituent represents an C ₆ -C ₂₀ aryl group.), A hydroxyl group or a halogen atom. R ^{1 to} R ³ , R ^{6 to} R ¹¹ , and R ^{14 to} R ¹⁶ are independent of each other and may be the same or different. Also, R ¹ and R ² , R ⁶ and R ⁷ , R ⁷ and R ⁸ , R ⁹ and R ¹⁰ , R ¹⁰ and R ¹¹ , R ¹⁵ and R ¹⁶ are cross-linked with each other to form C _{4 to} C _10. A saturated ring or an unsaturated ring may be formed. In the case of the ring, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom, or a group represented by the formula —N (B) — (wherein B Is a hydrogen atom or a C ₁ -C ₁₀ hydrocarbon group.) And may have a substituent. X is an oxygen atom, a sulfur atom or a nitrogen atom which may have a substituent.

The eleventh aspect of the present invention is the reaction of an enyne represented by the following general formula (26) in the presence of a ruthenium or molybdenum catalyst to generate a cyclic compound represented by the following general formula (27). Furthermore, it is a method for producing a biaryl compound represented by the following general formula (28) by causing thermal decomposition or reaction in the presence of an acid or a base.

In the general formula (26), R ^{1 to} R ¹⁶ are a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group that may have a substituent, or a C _{1 to} C that may have a substituent. ₂₀ alkoxy group, optionally substituted C ₆ -C ₂₀ aryloxy group, optionally substituted amino group, optionally substituted silyl group, substituted An optionally substituted alkylthio group (—SY ¹ , wherein Y ¹ represents an optionally substituted C ₁ -C ₂₀ alkyl group), an optionally substituted arylthio group (—SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), an optionally substituted alkylsulfonyl group (—SO ₂ Y ³ In the formula, Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group.), An optionally substituted arylsulfonyl group (—SO ₂ Y ⁴ , Y ⁴ is a substituted group Have shown a good C ₆ -C ₂₀ aryl group.), A hydroxyl group or a halogen atoms. R ^{1 to} R ¹⁶ are independent of each other and may be the same or different. R ¹ and R ² , R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ⁶ and R ⁸ , R ¹⁰ and R ¹¹ , R ¹¹ and R ¹² , R ¹² and R ¹³ , R ¹³ and R ¹⁴ , R ¹⁵ and R ¹⁶ may be bridged with each other to form a C _{4 to} C ₁₀ saturated or unsaturated ring, and in the case of the ring, an oxygen atom, a sulfur atom, a silicon atom , Tin atom, germanium atom or a group represented by the formula —N (B) — (wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group), and substituted It may have a group.

In the general formula (27), R ^{3 to} R ¹⁴ are a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group which may have a substituent, or a C _{1 to} C which may have a substituent. ₂₀ alkoxy group, optionally substituted C ₆ -C ₂₀ aryloxy group, optionally substituted amino group, optionally substituted silyl group, substituted An optionally substituted alkylthio group (—SY ¹ , wherein Y ¹ represents an optionally substituted C ₁ -C ₂₀ alkyl group), an optionally substituted arylthio group (—SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), an optionally substituted alkylsulfonyl group (—SO ₂ Y ³ In the formula, Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group.), An optionally substituted arylsulfonyl group (—SO ₂ Y ⁴ , Y ⁴ is a substituted group Have shown a good C ₆ -C ₂₀ aryl group.), A hydroxyl group or a halogen atoms. R ^{3 to} R ¹⁴ are independent of each other and may be the same or different. R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ⁶ and R ⁸ , R ¹⁰ and R ¹¹ , R ¹¹ and R ¹² , R ¹² and R ¹³ , R ¹³ and R ¹⁴ are Each may be bridged with each other to form a C _{4 to} C ₁₀ saturated or unsaturated ring, in the case of said rings, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom or a formula —N (B ) — (Wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) and may have a substituent.

In the above general formula (28), R ^{3 to} R ⁶ , R ⁸ and R ^{10 to} R ¹⁴ have a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group which may have a substituent, and a substituent. which may be C ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, which may have a substituent a silyl group which may have a substituent alkylthio group (-SY ^1, in the formula, Y ¹ is a good C ₁ -C ₂₀ alkyl group which may have a substituent.), a substituent have good arylthio group (-SY ^2, in the formula, Y ² is a good C ₆ -C ₂₀ aryl group which may have a substituent.), an alkyl which may have a substituent A sulfonyl group (—SO ₂ Y ³ , wherein Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group), an optionally substituted arylsulfonyl group (— SO ₂ Y ⁴ , where Y ⁴ represents an optionally substituted C ₆ -C ₂₀ aryl group.), A hydroxyl group or a halogen atom. R ^{3 to} R ⁶ , R ⁸ and R ^{10 to} R ¹⁴ are independent of each other and may be the same or different. R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ⁶ and R ⁸ , R ¹⁰ and R ¹¹ , R ¹¹ and R ¹² , R ¹² and R ¹³ , R ¹³ and R ¹⁴ are Each may be bridged with each other to form a C _{4 to} C ₁₀ saturated or unsaturated ring, in the case of said rings, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom or a formula —N (B ) — (Wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) and may have a substituent.

In a twelfth aspect of the present invention, a diaryl compound represented by the following general formula (29) is reacted in the presence of a ruthenium or molybdenum catalyst to produce a biaryl compound represented by the following general formula (30). Is the method.

In the general formula (29), R ^{1 to} R ⁶ and R ^{11 to} R ^{16 each} have a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group that may have a substituent, or a substituent. which may C ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, which may have a substituent silyl group, which may have a substituent alkylthio group (-SY ^1, in the formula, Y ¹ is a good C ₁ -C ₂₀ alkyl group which may have a substituent.), a substituent An optionally substituted arylthio group (—SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), an optionally substituted alkylsulfonyl group (-SO ₂ Y ^3, in the formula, Y ³ represents a good C ₁ -C ₂₀ alkyl group which may have a substituent.), which may have a substituent arylsulfonyl group (-SO ₂ Y ⁴ , where Y ⁴ represents an optionally substituted C ₆ -C ₂₀ aryl group), a hydroxyl group or a halogen atom. R ^{1 to} R ⁶ and R ^{11 to} R ¹⁶ are independent of each other and may be the same or different. R ¹ and R ² , R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ¹¹ and R ¹² , R ¹² and R ¹³ , R ¹³ and R ¹⁴ , R ¹⁵ and R ¹⁶ are Each may be bridged with each other to form a C _{4 to} C ₁₀ saturated or unsaturated ring, in the case of said rings, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom or a formula —N (B ) — (Wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) and may have a substituent. X is an oxygen atom, a sulfur atom or a nitrogen atom which may have a substituent.

In the general formula (30), R ^{3 to} R ⁶ and R ^{11 to} R ^{14 each} have a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group that may have a substituent, or a substituent. which may C ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, which may have a substituent silyl group, which may have a substituent alkylthio group (-SY ^1, in the formula, Y ¹ is a good C ₁ -C ₂₀ alkyl group which may have a substituent.), a substituent An optionally substituted arylthio group (—SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), an optionally substituted alkylsulfonyl group (-SO ₂ Y ^3, in the formula, Y ³ represents a good C ₁ -C ₂₀ alkyl group which may have a substituent.), which may have a substituent arylsulfonyl group (-SO ₂ Y ⁴ , where Y ⁴ represents an optionally substituted C ₆ -C ₂₀ aryl group), a hydroxyl group or a halogen atom. R ^{3 to} R ⁶ and R ^{11 to} R ¹⁴ are independent of each other and may be the same or different. R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ¹¹ and R ¹² , R ¹² and R ¹³ , R ¹³ and R ¹⁴ , R ¹⁵ and R ¹⁶ are cross-linked with each other. C _{4 to} C ₁₀ may form a saturated or unsaturated ring, and in the case of the ring, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom, or a group represented by the formula —N (B) — (Wherein B is a hydrogen atom or a C ₁ -C ₁₀ hydrocarbon group) and may have a substituent. X is an oxygen atom, a sulfur atom or a nitrogen atom which may have a substituent.

  As described above, the present invention can provide a production method for efficiently and simply obtaining biaryl compounds having various substitution modes.

  Hereinafter, embodiments for carrying out the present invention will be described in detail.

(First embodiment)
In the first embodiment of the present invention, an enyne represented by the following general formula (1) is reacted in the presence of a ruthenium or molybdenum catalyst to generate a cyclic compound represented by the following general formula (2), Furthermore, it is a method for producing a biaryl compound represented by the following general formula (3) by thermal decomposition or reaction in the presence of an acid or a base.

In the general formula (1), R ^{1 to} R ¹⁶ are a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group that may have a substituent, or a C _{1 to} C ₂₀ that may have a substituent. alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, which may have a substituent silyl group, substituted which may be an alkylthio group (-SY ^1, in the formula, Y ¹ is a good C ₁ -C ₂₀ alkyl group which may have a substituent.), which may have a substituent arylthio group ( -SY ^2, in the formula, Y ² is a good C ₆ -C ₂₀ aryl group which may have a substituent.), which may have a substituent alkylsulfonyl group (-SO ₂ Y ^3, In the formula, Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group.), An optionally substituted arylsulfonyl group (—SO ₂ Y ⁴ , wherein Y ⁴ has a substituent Can have represents an C ₆ -C ₂₀ aryl group.), A hydroxyl group or a halogen atom. R ^{1 to} R ¹⁶ are independent of each other and may be the same or different. R ¹ and R ² , R ³ and R ⁴ , R ⁴ and R ⁶ , R ⁶ and R ⁷ , R ⁷ and R ⁸ , R ⁹ and R ¹⁰ , R ¹⁰ and R ¹² , R ¹² and R ¹³ , R ¹³ and R ¹⁴ , and R ¹⁵ and R ¹⁶ may be bridged with each other to form a C _{4 to} C ₁₀ saturated or unsaturated ring, and in the case of the ring, an oxygen atom, a sulfur atom , silicon atom, tin atom, germanium atom or -N (B) - group (. where B is a hydrogen atom or a C ₁ -C ₁₀ hydrocarbon group) represented by may be interrupted by, and, It may have a substituent.

In the general formula (2), R ^{3 to} R ¹⁴ are each a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group that may have a substituent, or a C _{1 to} C ₂₀ that may have a substituent. Alkoxy group, C ₆ -C ₂₀ aryloxy group optionally having substituent, amino group optionally having substituent, silyl group optionally having substituent, having substituent which may be an alkylthio group (-SY ^1, in the formula, Y ¹ is a good C ₁ -C ₂₀ alkyl group which may have a substituent.), which may have a substituent arylthio group ( -SY ^2, in the formula, Y ² is a good C ₆ -C ₂₀ aryl group which may have a substituent.), which may have a substituent alkylsulfonyl group (-SO ₂ Y ^3, In the formula, Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group.), An optionally substituted arylsulfonyl group (—SO ₂ Y ⁴ , wherein Y ⁴ has a substituent Can have represents an C ₆ -C ₂₀ aryl group.), A hydroxyl group or a halogen atom. R ^{3 to} R ¹⁴ are independent of each other and may be the same or different. Also, R ³ and R ^4, R ⁴ and R ^6, R ⁶ and R ^7, R ⁷ and R ^8, R ⁹ and R ^10, R ¹⁰ and R ^12, R ¹² and R ^13, and R ¹³ and R ¹⁴ May be bridged with each other to form a C _{4 to} C ₁₀ saturated ring or unsaturated ring, and in the case of the ring, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom, or —N ( B) -. group (wherein B represented by may be interrupted by a hydrogen atom or a C ₁ -C ₁₀ hydrocarbon group), and may have a substituent.

In the general formula ^{(3), R 3, R} 4, R 6 ~R 10, R 12 ~R 14 is a hydrogen atom, which may have a substituent C ₁ -C ₂₀ hydrocarbon group, a substituent which may have a C ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, substituted An optionally substituted silyl group, an optionally substituted alkylthio group (-SY ¹ , wherein Y ¹ represents an optionally substituted C ₁ -C ₂₀ alkyl group), also an optionally substituted arylthio group (-SY ^2, in the formula, Y ² is a good C ₆ -C ₂₀ aryl group which may have a substituent.), have a substituent which may alkylsulfonyl group (-SO ₂ Y ^3, in the formula, Y ³ represents a good C ₁ -C ₂₀ alkyl group which may have a substituent.), an arylsulfonyl optionally having substituent group (-SO ₂ Y ^4, wherein , Y ⁴ represents a good C ₆ -C ₂₀ aryl group which may have a substituent.), A hydroxyl group or a halogen atom. R ^{3 to} R ¹⁴ are independent of each other and may be the same or different. Also, R ³ and R ^4, R ⁴ and R ^6, R ⁶ and R ^7, R ⁷ and R ^8, R ⁹ and R ^10, R ¹⁰ and R ^12, R ¹² and R ^13, and R ¹³ and R ¹⁴ May be bridged with each other to form a C _{4 to} C ₁₀ saturated ring or unsaturated ring, and in the case of the ring, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom, or —N ( B) -. group (wherein B represented by may be interrupted by a hydrogen atom or a C ₁ -C ₁₀ hydrocarbon group), and may have a substituent.

In the present specification and claims, the hydrocarbon group of the “C ₁ -C ₂₀ hydrocarbon group” may be a saturated or unsaturated acyclic group, or a saturated or unsaturated ring. It may be a formula. When the C _{1 to} C ₂₀ hydrocarbon group is acyclic, it may be linear or branched. "C ₁ -C ₂₀ hydrocarbon group" in the C ₁ -C ₂₀ alkyl group, C ₂ -C ₂₀ alkenyl group, C ₂ -C ₂₀ alkynyl group, C ₄ -C ₂₀ alkadienyl group, C ₆ -C ₂₀ aryl group, C ₆ -C ₂₀ alkylaryl group, C ₆ -C ₂₀ arylalkyl group, C ₃ -C ₂₀ cycloalkyl group, C ₃ -C ₂₀ cycloalkenyl group, (C ₃ ~C ₁₀ cycloalkyl) C etc. ₁ -C ₂₀ alkyl group.

In the present specification and claims, "C ₁ -C ₂₀ alkyl group" is preferably C ₁ -C ₁₀ alkyl group, more preferably a C ₁ -C ₆ alkyl group. Examples of alkyl groups include, but are not limited to, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, pentyl, hexyl, dodecanyl and the like.

In the present specification and claims, "C ₂ -C ₂₀ alkenyl group" is preferably C ₂ -C ₁₀ alkenyl group, more preferably a C ₂ -C ₆ alkenyl group. Examples of alkenyl groups include, but are not limited to, vinyl, allyl, propenyl, isopropenyl, 2-methyl-1-propenyl, 2-methylallyl, 2-butenyl and the like.

In the present specification and claims, the “C ₂ -C ₂₀ alkynyl group” is preferably C ₂ -C ₁₀ alkynyl group, and more preferably C ₂ -C ₆ alkynyl group. Examples of alkynyl groups include, but are not limited to, ethynyl, 2-propynyl, 2-butynyl, and the like.

In the present specification and claims, "C ₄ -C ₂₀ alkyldienyl group" is preferably C ₄ -C ₁₀ alkadienyl group, are C ₄ -C ₆ alkadienyl group More preferably. Examples of alkyldienyl groups include, but are not limited to, 1,3-butadienyl.

In the present specification and claims, the “C ₆ -C ₂₀ aryl group” is preferably a C ₆ -C ₁₀ aryl group. Examples of the aryl group include, but are not limited to, phenyl, 1-naphthyl, 2-naphthyl, indenyl, biphenylyl, anthryl, phenanthryl and the like.

In the present specification and claims, the “C ₆ -C ₂₀ alkylaryl group” is preferably a C ₆ -C ₁₂ alkylaryl group. Examples of alkylaryl groups include, but are not limited to, o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, o-cumenyl, m-cumenyl, p-cumenyl, mesityl, and the like. Can do.

In the present specification and claims, the “C ₆ -C ₂₀ arylalkyl group” is preferably a C ₆ -C ₁₂ arylalkyl group. Examples of arylalkyl groups include, but are not limited to, benzyl, phenethyl, diphenylmethyl, triphenylmethyl, 1-naphthylmethyl, 2-naphthylmethyl, 2,2-diphenylmethyl, 3-phenylpropyl, 4-phenyl Examples include phenylbutyl and 5-phenylpentyl.

In the present specification and claims, the “C ₃ -C ₂₀ cycloalkyl group” is preferably a C ₃ -C ₁₀ cycloalkyl group. Examples of cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like.

In the present specification and claims, the “C ₃ -C ₂₀ cycloalkenyl group” is preferably a C ₃ -C ₁₀ cycloalkenyl group. Examples of cycloalkenyl groups include, but are not limited to, cyclopropenyl, cyclobutenyl, 2-cyclopenten-1-yl, 2-cyclohexen-1-yl, 3-cyclohexen-1-yl, and the like.

In the present specification and claims, the “C ₁ -C ₂₀ alkoxy group” is preferably a C ₁ -C ₁₀ alkoxy group, and more preferably a C ₁ -C ₆ alkoxy group. Examples of alkoxy groups include, but are not limited to, methoxy, ethoxy, propoxy, butoxy, pentyloxy and the like.

In the present specification and claims, the “C ₆ -C ₂₀ aryloxy group” is preferably a C ₆ -C ₁₀ aryloxy group. Examples of aryloxy groups include, but are not limited to, phenyloxy, naphthyloxy, biphenylyloxy, and the like.

In the present specification and claims, “alkylthio group (—SY ¹ , wherein Y ¹ represents an optionally substituted C ₁ -C ₂₀ alkyl group)” and “alkylsulfonyl” In the group (—SO ₂ Y ³ , wherein Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group) ”, Y ¹ and Y ³ are C ₁ -C ₁₀ alkyl. it is preferably a group, more preferably a C ₁ -C ₆ alkyl group. Examples of alkyl groups include, but are not limited to, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, pentyl, hexyl, dodecanyl and the like.

Further, in the present specification and claims, “C ₁ -C ₂₀ hydrocarbon group”, “C ₁ -C ₂₀ alkoxy group”, “C ₆ -C ₂₀ aryloxy group” represented by R ^{1 to} R ¹⁶ , “Amino group”, “silyl group”, “alkylthio group”, “arylthio group”, “alkylsulfonyl group”, and “arylsulfonyl group” may have a substituent introduced therein. Examples of the substituent include a C _{1 to} C ₁₀ hydrocarbon group (for example, methyl, ethyl, propyl, butyl, phenyl, naphthyl, indenyl, tolyl, xylyl, benzyl, etc.), a C _{1 to} C ₁₀ alkoxy group (for example, , Methoxy, ethoxy, propoxy, butoxy, etc.), C ₆ -C ₁₀ aryloxy groups (eg, phenyloxy, naphthyloxy, biphenyloxy, etc.) amino groups, hydroxyl groups, halogen atoms (eg, fluorine, chlorine, bromine, iodine) Or a silyl group etc. can be mentioned. In this case, one or more substituents may be introduced at substitutable positions, and preferably 1 to 6 substituents may be introduced. When the number of substituents is 2 or more, each substituent may be the same or different.

  In the present specification and claims, examples of the “optionally substituted amino group” include, but are not limited to, amino, dimethylamino, methylamino, methylphenylamino, phenyl There are amino and the like.

  Further, in the present specification and claims, examples of “optionally substituted silyl group” include, but are not limited to, trimethylsilyl, triethylsilyl, trimethoxysilyl, triethoxysilyl, Examples include diphenylmethylsilyl, triphenylsilyl, triphenoxysilyl, dimethylmethoxysilyl, dimethylphenoxysilyl, methylmethoxyphenyl, and the like.

In the present specification and claims, substituents represented by R ^{1 to} R ¹⁶ may be bridged with each other to form a C _{4 to} C ₂₀ saturated ring or an unsaturated ring. The ring formed by these substituents is preferably a 4- to 12-membered ring, more preferably a 4- to 6-membered ring. This ring may be an aromatic ring such as a benzene ring or an aliphatic ring. One or more rings may be further formed on the ring formed by these substituents. It said saturated ring or unsaturated ring, oxygen atom, sulfur atom, silicon atom, tin atom, germanium atom or -N (B) - is a hydrogen atom or a C ₁ is (B represented by -C ₂₀ hydrocarbon group. ) May be interrupted. That is, the saturated ring or unsaturated ring may be a heterocyclic ring. And you may have a substituent. The unsaturated ring may be an aromatic ring such as a benzene ring. B is preferably a hydrogen atom or a C ₁ -C ₁₀ hydrocarbon group, more preferably a hydrogen atom or a C ₁ -C ₇ hydrocarbon group, B is a hydrogen atom, C ₁ -C ₃ alkyl group Still more preferably, it is a phenyl group or a benzyl group. This saturated ring or unsaturated ring may have a substituent, for example, a C _{1 to} C ₁₀ hydrocarbon group (for example, methyl, ethyl, propyl, butyl group), a C _{1 to} C ₁₀ alkoxy group ( For example, methoxy, ethoxy, propoxy, butoxy, etc.), C ₆ -C ₁₀ aryloxy groups (eg, phenyloxy, naphthyloxy, biphenyloxy etc.), amino groups, hydroxyl groups, halogen atoms (eg, fluorine, chlorine, bromine, Substituents such as iodine) or silyl groups may be introduced.

  In the present specification and claims, the “aromatic ring” includes a monocyclic aromatic ring and a polycyclic aromatic ring. Examples of the “monocyclic aromatic ring” include a benzene ring, a 5-membered or 6-membered heterocyclic ring. Examples of the “5-membered or 6-membered heterocycle” include furan, thiophene, pyrrole, pyran, thiopyran, pyridine, thiazol, imidazole, pyrimidine, 1,3,5-triazine and the like. . Examples of the “polycyclic aromatic ring” include a polycyclic aromatic hydrocarbon and a polycyclic heteroaromatic ring. Examples of the “polycyclic heterohydrocarbon” include biphenyl, triphenyl, naphthalene, indene, anthracene, phenanthrene and the like. Examples of the “polycyclic heteroaromatic ring” include indol, quinoline, purine and the like.

  In the present embodiment, the “ruthenium or molybdenum catalyst” refers to a catalyst having a ruthenium or molybdenum compound and a phosphine ligand, carbene ligand, alkoxy ligand, or halogen ligand. Specific examples include, but are not limited to, benzylidenebis (tricyclohexylphosphine) dichlororuthenium and (1,3-bis- (2,4,6-trimethylphenyl) -2-imidazolidinylidene) dichloro (phenylmethylene)- (Tricyclohexylphosphine) dichlororuthenium and the like.

(Second embodiment)
In the second embodiment of the present invention, a biaryl compound represented by the general formula (5) is produced by reacting a dienein represented by the following general formula (4) in the presence of a ruthenium or molybdenum catalyst. Is the way.

In the above general formula (4), R ^{1 to} R ⁴ , R ^{7 to} R ¹⁰ , R ^{13 to} R ¹⁶ are hydrogen atoms and optionally substituted C _{1 to} C ₂₀ hydrocarbon groups, substituted Yes it may have a group C ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, a substituent An optionally substituted silyl group and an optionally substituted alkylthio group (—SY ¹ , wherein Y ¹ represents an optionally substituted C _{1 to} C ₂₀ alkyl group). , An optionally substituted arylthio group (—SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), has a substituent An optionally substituted alkylsulfonyl group (—SO ₂ Y ³ , wherein Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group), an optionally substituted aryl Sulfonyl group (-SO ₂ Y ⁴ In the formula, Y ⁴ represents an optionally substituted C ₆ -C ₂₀ aryl group.), A hydroxyl group, or a halogen atom. R ^{1 to} R ⁴ , R ^{7 to} R ¹⁰ , and R ^{13 to} R ¹⁶ are independent of each other and may be the same or different. R ¹ and R ² , R ³ and R ⁴ , R ⁷ and R ⁸ , R ⁹ and R ¹⁰ , R ¹³ and R ¹⁴ , R ¹⁵ and R ¹⁶ are cross-linked with each other to be saturated with C _{4 to} C _10. A ring or an unsaturated ring may be formed, and in the case of the ring, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom, or a group represented by the formula —N (B) — (wherein B is A hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group.) And may have a substituent. X is an oxygen atom, a sulfur atom or a nitrogen atom which may have a substituent.

Further, in the above general formula ^{(5), R 3, R} 4, R 7 ~R 10, R 13, R 14, are hydrogen atoms, which may have a substituent C ₁ -C ₂₀ hydrocarbon group, which may have a substituent C ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, a substituent A silyl group which may have, and an alkylthio group which may have a substituent (—SY ¹ , wherein Y ¹ represents a C _{1 to} C ₂₀ alkyl group which may have a substituent. ), An optionally substituted arylthio group (—SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), has a substituent An optionally substituted alkylsulfonyl group (—SO ₂ Y ³ , wherein Y ³ represents a C _{1 to} C ₂₀ alkyl group which may have a substituent), and may have a substituent. Arylsulfonyl group (—SO ₂ Y ⁴ , wherein Y ⁴ represents an optionally substituted C ₆ -C ₂₀ aryl group), a hydroxyl group, or a halogen atom. R ³ , R ⁴ , R ^{7 to} R ¹⁰ , R ¹³ , and R ¹⁴ are independent of each other and may be the same or different. R ³ and R ⁴ , R ⁷ and R ⁸ , R ⁹ and R ¹⁰ , R ¹³ and R ¹⁴ may be bridged with each other to form a C _{4 to} C ₁₀ saturated or unsaturated ring, In the case of the ring, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom or a group represented by the formula —N (B) — (wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) May be interrupted and may have a substituent. X is an oxygen atom, a sulfur atom or a nitrogen atom which may have a substituent.

(Third embodiment)
In the third embodiment of the present invention, an enyne represented by the following general formula (6) is reacted in the presence of a ruthenium or molybdenum catalyst to generate a cyclic compound represented by the following general formula (7). And a biaryl compound represented by the following general formula (8) by further thermal decomposition or reaction in the presence of an acid or a base.

In the general formula (6), R ^{1 to} R ¹⁶ are a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group that may have a substituent, or a C ₁ to C that may have a substituent. C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, which may have a substituent silyl group, a substituent have alkylthio group (-SY ^1, shown in the formula, Y ¹ is an optionally C ₁ -C ₂₀ alkyl group which may have a substituent.) may arylthio optionally having substituent A group (—SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), an optionally substituted alkylsulfonyl group (—SO ₂ Y ³ , wherein Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group.), An optionally substituted arylsulfonyl group (—SO ₂ Y ⁴ , , Y ⁴ is a substituted group Have shown even better C ₆ -C ₂₀ aryl group optionally.), A hydroxyl group, or a halogen atom. R ^{1 to} R ¹⁶ are independent of each other and may be the same or different. R ¹ and R ² , R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁷ , R ⁷ and R ⁸ , R ⁹ and R ¹¹ , R ¹¹ and R ¹² , R ¹² and R ¹³ , R ¹³ and R ¹⁴ , R ¹⁵ and R ¹⁶ may be bridged with each other to form a C _{4 to} C ₁₀ saturated or unsaturated ring, and in the case of the ring, an oxygen atom, a sulfur atom, silicon atom, tin atom, germanium atom or the formula -N (B) - group (. wherein, B is a hydrogen atom or a C ₁ -C ₁₀ hydrocarbon group) represented by may be interrupted by, and, It may have a substituent.

In the general formula (7), R ^{3 to} R ¹⁴ are a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group that may have a substituent, or a C _{1 to} C that may have a substituent. ₂₀ alkoxy group, optionally substituted C ₆ -C ₂₀ aryloxy group, optionally substituted amino group, optionally substituted silyl group, substituted An optionally substituted alkylthio group (—SY ¹ , wherein Y ¹ represents an optionally substituted C ₁ -C ₂₀ alkyl group), an optionally substituted arylthio group (—SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), an optionally substituted alkylsulfonyl group (—SO ₂ Y ³ In the formula, Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group.), An optionally substituted arylsulfonyl group (—SO ₂ Y ⁴ , Y ⁴ is a substituent And shows also good C ₆ -C ₂₀ aryl group optionally.), A hydroxyl group, or a halogen atom. R ^{3 to} R ¹⁴ are independent of each other and may be the same or different. R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁷ , R ⁷ and R ⁸ , R ⁹ and R ¹¹ , R ¹¹ and R ¹² , R ¹² and R ¹³ , R ¹³ and R ¹⁴ are , respectively, in the case of C ₄ -C ₁₀ may form a saturated or unsaturated ring, wherein said ring crosslinked to each other, an oxygen atom, a sulfur atom, a silicon atom, tin atom, germanium atom or the formula -N ( B) — may be interrupted by a group represented by the formula (wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) and may have a substituent.

In the above general formula (8), R ^{3 to} R ⁵ , R ^{7 to} R ⁹ , and R ^{11 to} R ¹⁴ are a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group that may have a substituent, and a substituent. Yes it may have a group C ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, a substituent An optionally substituted silyl group and an optionally substituted alkylthio group (—SY ¹ , wherein Y ¹ represents an optionally substituted C _{1 to} C ₂₀ alkyl group). , An optionally substituted arylthio group (—SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), has a substituent An optionally substituted alkylsulfonyl group (—SO ₂ Y ³ , wherein Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group), an optionally substituted aryl a sulfonyl group (-SO ₂ Y ⁴ In the formula, Y ⁴ is a good C ₆ -C ₂₀ aryl group which may have a substituent.), A hydroxyl group, or a halogen atom. R ^{3 to} R ⁵ , R ^{7 to} R ⁹ , and R ^{11 to} R ¹⁴ are independent of each other and may be the same or different. R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁷ , R ⁷ and R ⁸ , R ⁹ and R ¹¹ , R ¹¹ and R ¹² , R ¹² and R ¹³ , R ¹³ and R ¹⁴ are , respectively, in the case of C ₄ -C ₁₀ may form a saturated or unsaturated ring, wherein said ring crosslinked to each other, an oxygen atom, a sulfur atom, a silicon atom, tin atom, germanium atom or the formula -N ( B) — may be interrupted by a group represented by the formula (wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) and may have a substituent.

(Fourth embodiment)
According to a fourth embodiment of the present invention, there is provided a biaryl compound represented by the general formula (10), wherein the dienein represented by the following general formula (9) is reacted in the presence of a ruthenium or molybdenum catalyst. It is a method of manufacturing.

In the above general formula (9), R ^{1 to} R ⁵ , R ⁸ , R ⁹ and R ^{12 to} R ¹⁶ are hydrogen atoms, C _{1 to} C ₂₀ hydrocarbon groups which may have a substituent, and substituents. Yes it may have a group C ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, a substituent An optionally substituted silyl group and an optionally substituted alkylthio group (—SY ¹ , wherein Y ¹ represents an optionally substituted C _{1 to} C ₂₀ alkyl group). , An optionally substituted arylthio group (—SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), has a substituent An optionally substituted alkylsulfonyl group (—SO ₂ Y ³ , wherein Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group), an optionally substituted aryl a sulfonyl group (-SO ₂ Y ⁴ In the formula, Y ⁴ is a good C ₆ -C ₂₀ aryl group which may have a substituent.), A hydroxyl group, or a halogen atom. R ^{1 to} R ⁵ , R ⁸ , R ⁹ and R ^{12 to} R ¹⁶ are independent of each other and may be the same or different. R ¹ and R ² , R ³ and R ⁴ , R ⁴ and R ⁵ , R ¹² and R ¹³ , R ¹³ and R ¹⁴ , R ¹⁵ and R ¹⁶ are cross-linked with each other to be saturated with C _{4 to} C _10. A ring or an unsaturated ring may be formed, and in the case of the ring, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom, or a group represented by the formula —N (B) — (wherein B is A hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group.) And may have a substituent. X is an oxygen atom, a sulfur atom, or a nitrogen atom that may have a substituent.

In the general formula (10), R ^{3 to} R ⁵ , R ⁸ , R ⁹ , and R ^{12 to} R ¹⁴ are a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group that may have a substituent, which may have a substituent C ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, a substituent A silyl group which may have, and an alkylthio group which may have a substituent (—SY ¹ , wherein Y ¹ represents a C _{1 to} C ₂₀ alkyl group which may have a substituent. ), An optionally substituted arylthio group (—SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), has a substituent An optionally substituted alkylsulfonyl group (—SO ₂ Y ³ , wherein Y ³ represents a C _{1 to} C ₂₀ alkyl group which may have a substituent), and may have a substituent. Arylsulfonyl group (—SO ₂ Y ⁴ , wherein Y ⁴ represents a C ₆ -C ₂₀ aryl group which may have a substituent), a hydroxyl group, or a halogen atom. R ^{3 to} R ⁵ , R ⁸ , R ⁹ and R ^{12 to} R ¹⁴ are independent of each other and may be the same or different. R ³ and R ⁴ , R ⁴ and R ⁵ , R ¹² and R ¹³ , R ¹³ and R ¹⁴ may be bridged with each other to form a C _{4 to} C ₁₀ saturated or unsaturated ring, In the case of the ring, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom or a group represented by the formula —N (B) — (wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) May be interrupted and may have a substituent. X is an oxygen atom, a sulfur atom, or a nitrogen atom that may have a substituent.

(Fifth embodiment)
In the fifth embodiment of the present invention, a cyclic compound represented by the general formula (12) is generated by reacting an enyne represented by the following general formula (11) in the presence of a ruthenium or molybdenum catalyst. And a biaryl compound represented by the following general formula (13) is produced by thermal decomposition or reaction in the presence of an acid or a base.

In the general formula (11), R ^{1 to} R ¹⁶ are a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group that may have a substituent, or a C _{1 to} C that may have a substituent. ₂₀ alkoxy group, optionally substituted C ₆ -C ₂₀ aryloxy group, optionally substituted amino group, optionally substituted silyl group, substituted An optionally substituted alkylthio group (—SY ¹ , wherein Y ¹ represents an optionally substituted C ₁ -C ₂₀ alkyl group), an optionally substituted arylthio group (—SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), an optionally substituted alkylsulfonyl group (—SO ₂ Y ³ In the formula, Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group.), An optionally substituted arylsulfonyl group (—SO ₂ Y ⁴ , Y ⁴ is a substituted group Have shown even better C ₆ -C ₂₀ aryl group optionally.), A hydroxyl group, or a halogen atom. R ^{1 to} R ¹⁶ are independent of each other and may be the same or different. R ¹ and R ² , R ³ and R ⁵ , R ⁵ and R ⁶ , R ⁶ and R ⁷ , R ⁷ and R ⁸ , R ⁹ and R ¹⁰ , R ¹⁰ and R ¹¹ , R ¹¹ and R ¹³ , R ¹³ and R ¹⁴ , R ¹⁵ and R ¹⁶ may be bridged with each other to form a C _{4 to} C ₁₀ saturated or unsaturated ring, and in the case of the ring, an oxygen atom, a sulfur atom, silicon atom, tin atom, germanium atom or the formula -N (B) - group (. wherein, B is a hydrogen atom or a C ₁ -C ₁₀ hydrocarbon group) represented by may be interrupted by, and, It may have a substituent.

In the general formula (12), R ^{3 to} R ¹⁴ are each a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group which may have a substituent, or a C ₁ to which may have a substituent. C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, which may have a substituent silyl group, a substituent have alkylthio group (-SY ^1, shown in the formula, Y ¹ is an optionally C ₁ -C ₂₀ alkyl group which may have a substituent.) may arylthio optionally having substituent A group (—SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), an optionally substituted alkylsulfonyl group (—SO ₂ Y ³ , wherein Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group.), An optionally substituted arylsulfonyl group (—SO ₂ Y ⁴ , , Y ⁴ is a substituted Even when the have shown a good C ₆ -C ₂₀ aryl group.), A hydroxyl group, or a halogen atom. R ^{3 to} R ¹⁴ are independent of each other and may be the same or different. R ³ and R ⁵ , R ⁵ and R ⁶ , R ⁶ and R ⁷ , R ⁷ and R ⁸ , R ⁹ and R ¹⁰ , R ¹⁰ and R ¹¹ , R ¹¹ and R ¹³ , R ¹³ and R ¹⁴ are , respectively, in the case of C ₄ -C ₁₀ may form a saturated or unsaturated ring, wherein said ring crosslinked to each other, an oxygen atom, a sulfur atom, a silicon atom, tin atom, germanium atom or the formula -N ( B) — may be interrupted by a group represented by the formula (wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) and may have a substituent.

In the general formula (13), R ³ , R ^{5 to} R ¹¹ , R ¹³ , and R ¹⁴ have a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group that may have a substituent, and a substituent. and C ₁ optionally -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, substituted An optionally substituted silyl group, an optionally substituted alkylthio group (—SY ¹ , wherein Y ¹ represents an optionally substituted C ₁ -C ₂₀ alkyl group), a substituent. An arylthio group (-SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), may have a substituent An alkylsulfonyl group (—SO ₂ Y ³ , wherein Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group), an optionally substituted arylsulfonyl group ( -SO ₂ Y ^4, In, Y ⁴ represents a good C ₆ -C ₂₀ aryl group which may have a substituent.), A hydroxyl group, or a halogen atom. R ³ , R ^{5 to} R ¹¹ , R ¹³ and R ¹⁴ are independent of each other and may be the same or different. R ³ and R ⁵ , R ⁵ and R ⁶ , R ⁶ and R ⁷ , R ⁷ and R ⁸ , R ⁹ and R ¹⁰ , R ¹⁰ and R ¹¹ , R ¹¹ and R ¹³ , R ¹³ and R ¹⁴ are , respectively, in the case of C ₄ -C ₁₀ may form a saturated or unsaturated ring, wherein said ring crosslinked to each other, an oxygen atom, a sulfur atom, a silicon atom, tin atom, germanium atom or the formula -N ( B) — may be interrupted by a group represented by the formula (wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) and may have a substituent.

(Sixth embodiment)
In the sixth embodiment of the present invention, a diarylyne represented by the following general formula (14) is reacted in the presence of a ruthenium or molybdenum catalyst to produce a biaryl compound represented by the following general formula (15). Is the method.

In the general formula (14), R ^{1 to} R ³ , R ^{6 to} R ¹¹ , and R ^{14 to} R ¹⁶ are a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group which may have a substituent, and a substituent. which may have a C ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, substituted An optionally substituted silyl group, an optionally substituted alkylthio group (-SY ¹ , wherein Y ¹ represents an optionally substituted C ₁ -C ₂₀ alkyl group), also an optionally substituted arylthio group (-SY ^2, in the formula, Y ² is a good C ₆ -C ₂₀ aryl group which may have a substituent.), have a substituent which may alkylsulfonyl group (-SO ₂ Y ^3, in the formula, Y ³ represents a good C ₁ -C ₂₀ alkyl group which may have a substituent.), an arylsulfonyl optionally having substituent group (-SO ₂ Y ⁴ In the formula, Y ⁴ is a good C ₆ -C ₂₀ aryl group which may have a substituent.), A hydroxyl group or a halogen atom. R ^{1 to} R ³ , R ^{6 to} R ¹¹ , and R ^{14 to} R ¹⁶ are independent of each other and may be the same or different. R ¹ and R ² , R ⁶ and R ⁷ , R ⁷ and R ⁸ , R ⁹ and R ¹⁰ , R ¹⁰ and R ¹¹ , R ¹⁵ and R ¹⁶ are cross-linked with each other to be saturated with C _{4 to} C _10. A ring or an unsaturated ring may be formed, and in the case of the ring, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom, or a group represented by the formula —N (B) — (wherein B is A hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group.) And may have a substituent. X is an oxygen atom, a sulfur atom or a nitrogen atom which may have a substituent.

In the general formula (15), R ³ , R ^{6 to} R ¹¹ and R ¹⁴ may have a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group which may have a substituent, or a substituent. good C ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, a silyl group, which may have a substituent , which may have a substituent alkylthio group (-SY ^1, wherein, Y ¹ is. showing a good C ₁ -C ₂₀ alkyl group which may have a substituent), have a substituent An optionally substituted arylthio group (—SY ² , wherein Y ² represents an optionally substituted C _{6 to} C ₂₀ aryl group), an optionally substituted alkylsulfonyl group ( —SO ₂ Y ³ , wherein Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group), and optionally substituted arylsulfonyl group (—SO ₂ Y ^4, in the formula, Y ⁴ May have a substituent represents an C ₆ -C ₂₀ aryl group.), A hydroxyl group or a halogen atom. R ³ , R ^{6 to} R ¹¹ and R ¹⁴ are independent of each other and may be the same or different. R ⁶ and R ⁷ , R ⁷ and R ⁸ , R ⁹ and R ¹⁰ , R ¹⁰ and R ¹¹ may be bridged with each other to form a C _{4 to} C ₁₀ saturated or unsaturated ring, In the case of the ring, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom or a group represented by the formula —N (B) — (wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) May be interrupted and may have a substituent. X is an oxygen atom, a sulfur atom or a nitrogen atom which may have a substituent.

(Seventh embodiment)
In the seventh embodiment of the present invention, an enyne represented by the following general formula (16) is reacted in the presence of a ruthenium or molybdenum catalyst to generate a cyclic compound represented by the following general formula (17). And a biaryl compound represented by the following general formula (18) is produced by thermal decomposition or reaction in the presence of an acid or a base.

In the general formula (16), R ^{1 to} R ¹⁶ are a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group that may have a substituent, or a C _{1 to} C that may have a substituent. ₂₀ alkoxy group, optionally substituted C ₆ -C ₂₀ aryloxy group, optionally substituted amino group, optionally substituted silyl group, substituted An optionally substituted alkylthio group (—SY ¹ , wherein Y ¹ represents an optionally substituted C ₁ -C ₂₀ alkyl group), an optionally substituted arylthio group (—SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), an optionally substituted alkylsulfonyl group (—SO ₂ Y ³ In the formula, Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group.), An optionally substituted arylsulfonyl group (—SO ₂ Y ⁴ , Y ⁴ is a substituted group Have shown a good C ₆ -C ₂₀ aryl group.), There Oh a hydroxyl group or a halogen atom. R ^{1 to} R ¹⁶ are independent of each other and may be the same or different. R ¹ and R ² , R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ⁶ and R ⁸ , R ¹⁰ and R ¹¹ , R ¹¹ and R ¹² , R ¹² and R ¹³ , R ¹³ and R ¹⁴ , R ¹⁵ and R ¹⁶ may be bridged with each other to form a C _{4 to} C ₁₀ saturated or unsaturated ring, and in the case of the ring, an oxygen atom, a sulfur atom, a silicon atom , Tin atom, germanium atom or a group represented by the formula —N (B) — (wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group), and substituted It may have a group. )

In the general formula (17), R ^{3 to} R ¹⁴ are each a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group that may have a substituent, or a C _{1 to} C ₂₀ that may have a substituent. alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, which may have a substituent silyl group, substituted which may be an alkylthio group (-SY ^1, in the formula, Y ¹ is a good C ₁ -C ₂₀ alkyl group which may have a substituent.), which may have a substituent arylthio group ( -SY ^2, in the formula, Y ² is a good C ₆ -C ₂₀ aryl group which may have a substituent.), which may have a substituent alkylsulfonyl group (-SO ₂ Y ^3, In the formula, Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group.), An optionally substituted arylsulfonyl group (—SO ₂ Y ⁴ , wherein Y ⁴ have a substituent Even though showing a good C ₆ -C ₂₀ aryl group.), There Oh a hydroxyl group or a halogen atom. R ^{3 to} R ¹³ are independent of each other and may be the same or different. R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ⁶ and R ⁸ , R ¹⁰ and R ¹¹ , R ¹¹ and R ¹² , R ¹² and R ¹³ , R ¹³ and R ¹⁴ are Each may be bridged with each other to form a C _{4 to} C ₁₀ saturated or unsaturated ring, in the case of said rings, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom or a formula —N (B ) — (Wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) and may have a substituent.

In the general formula (18), R ^{3 to} R ⁶ , R ⁸ and R ^{10 to} R ¹⁴ have a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group which may have a substituent, and a substituent. which may be C ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, which may have a substituent a silyl group which may have a substituent alkylthio group (-SY ^1, in the formula, Y ¹ is a good C ₁ -C ₂₀ alkyl group which may have a substituent.), a substituent have good arylthio group (-SY ^2, in the formula, Y ² is a good C ₆ -C ₂₀ aryl group which may have a substituent.), an alkyl which may have a substituent A sulfonyl group (—SO ₂ Y ³ , wherein Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group), an optionally substituted arylsulfonyl group (— SO ₂ Y ⁴ , where Y ⁴ represents an optionally substituted C ₆ -C ₂₀ aryl group.), A hydroxyl group or a halogen atom. R ^{3 to} R ⁶ , R ⁸ and R ^{10 to} R ¹⁴ are independent of each other and may be the same or different. R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ⁶ and R ⁸ , R ¹⁰ and R ¹¹ , R ¹¹ and R ¹² , R ¹² and R ¹³ , R ¹³ and R ¹⁴ are Each may be bridged with each other to form a C _{4 to} C ₁₀ saturated or unsaturated ring, in the case of said rings, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom or a formula —N (B ) — (Wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) and may have a substituent.

(Eighth embodiment)
The eighth embodiment of the present invention is a method for producing a biaryl compound represented by the following general formula (20) by reacting a dienein represented by the general formula (19) in the presence of a ruthenium or molybdenum catalyst. It is.

In the general formula ^{(19), R 1 ~R 6} , R 11 ~R 16 is hydrogen atom, which may have a substituent C ₁ -C ₂₀ hydrocarbon group, which may have a substituent good C ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, a silyl group, which may have a substituent , which may have a substituent alkylthio group (-SY ^1, wherein, Y ¹ is. showing a good C ₁ -C ₂₀ alkyl group which may have a substituent), have a substituent An optionally substituted arylthio group (—SY ² , wherein Y ² represents an optionally substituted C _{6 to} C ₂₀ aryl group), an optionally substituted alkylsulfonyl group ( —SO ₂ Y ³ , wherein Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group), and optionally substituted arylsulfonyl group (—SO ₂ Y ^4: in the formula, Y ⁴ Have a substituent represents an C ₆ -C ₂₀ aryl group.), A hydroxyl group or a halogen atom. R ^{1 to} R ⁶ and R ^{11 to} R ¹⁶ are independent of each other and may be the same or different. R ¹ and R ² , R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ¹¹ and R ¹² , R ¹² and R ¹³ , R ¹³ and R ¹⁴ , R ¹⁵ and R ¹⁶ are Each may be bridged with each other to form a C _{4 to} C ₁₀ saturated or unsaturated ring, in the case of said rings, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom or a formula —N (B ) — (Wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) and may have a substituent. X is an oxygen atom; a sulfur atom; or a nitrogen atom that may have a substituent.

In the general formula ^{(20), R 3 ~R 6} , R 11 ~R 14 is a hydrogen atom, which may have a substituent C ₁ -C ₂₀ hydrocarbon group, which may have a substituent good C ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, a silyl group, which may have a substituent , which may have a substituent alkylthio group (-SY ^1, wherein, Y ¹ is. showing a good C ₁ -C ₂₀ alkyl group which may have a substituent), have a substituent An optionally substituted arylthio group (—SY ² , wherein Y ² represents an optionally substituted C _{6 to} C ₂₀ aryl group), an optionally substituted alkylsulfonyl group ( —SO ₂ Y ³ , wherein Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group), and optionally substituted arylsulfonyl group (—SO ₂ Y ^4: in the formula, Y ⁴ Have a substituent represents an C ₆ -C ₂₀ aryl group.), A hydroxyl group or a halogen atom. R ^{3 to} R ⁶ and R ^{11 to} R ¹⁴ are independent of each other and may be the same or different. R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ¹¹ and R ¹² , R ¹² and R ¹³ , R ¹³ and R ¹⁴ are each cross-linked and C _{4 to} C ₁₀ saturated. A ring or an unsaturated ring may be formed, and in the case of the ring, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom, or a group represented by the formula —N (B) — (wherein B is A hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group.) And may have a substituent. X is an oxygen atom; a sulfur atom; or a nitrogen atom that may have a substituent.

(Ninth embodiment)
In the ninth embodiment of the present invention, an enyne represented by the following general formula (21) is reacted in the presence of a ruthenium or molybdenum catalyst to generate a cyclic compound represented by the following general formula (22). And a method for producing a biaryl compound represented by the following general formula (23) by further thermal decomposition or reaction in the presence of an acid or a base.

In the general formula (21), R ¹ ~R ¹⁶ is hydrogen atom, which may have a substituent C ₁ -C ₂₀ hydrocarbon group which may have a substituent C ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, which may have a substituent silyl group, substituted which may be an alkylthio group (-SY ^1, in the formula, Y ¹ is a good C ₁ -C ₂₀ alkyl group which may have a substituent.), which may have a substituent arylthio group ( -SY ^2, in the formula, Y ² is a good C ₆ -C ₂₀ aryl group which may have a substituent.), which may have a substituent alkylsulfonyl group (-SO ₂ Y ^3, In the formula, Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group.), An optionally substituted arylsulfonyl group (—SO ₂ Y ⁴ , wherein Y ⁴ have a substituent Even though showing a good C ₆ -C ₂₀ aryl group.), A hydroxyl group or a halogen atom. R ^{1 to} R ¹⁶ are independent of each other and may be the same or different. R ¹ and R ² , R ³ and R ⁵ , R ⁵ and R ⁶ , R ⁶ and R ⁷ , R ⁷ and R ⁸ , R ⁹ and R ¹⁰ , R ¹⁰ and R ¹¹ , R ¹¹ and R ¹³ , R ¹³ and R ¹⁴ , R ¹⁵ and R ¹⁶ may be bridged with each other to form a C _{4 to} C ₁₀ saturated or unsaturated ring, and in the case of the ring, an oxygen atom, a sulfur atom, silicon atom, tin atom, germanium atom or the formula -N (B) - group (. wherein, B is a hydrogen atom or a C ₁ -C ₁₀ hydrocarbon group) represented by may be interrupted by, and, It may have a substituent.

In the general formula (22), R ^{3 to} R ¹⁴ are a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group that may have a substituent, or a C _{1 to} C ₂₀ that may have a substituent. alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, which may have a substituent silyl group, substituted which may be an alkylthio group (-SY ^1, in the formula, Y ¹ is a good C ₁ -C ₂₀ alkyl group which may have a substituent.), which may have a substituent arylthio group ( -SY ^2, in the formula, Y ² is a good C ₆ -C ₂₀ aryl group which may have a substituent.), which may have a substituent alkylsulfonyl group (-SO ₂ Y ^3, In the formula, Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group.), An optionally substituted arylsulfonyl group (—SO ₂ Y ⁴ , wherein Y ⁴ have a substituent Even though showing a good C ₆ -C ₂₀ aryl group.), A hydroxyl group or a halogen atom. R ^{3 to} R ¹⁴ are independent of each other and may be the same or different. R ³ and R ⁵ , R ⁵ and R ⁶ , R ⁶ and R ⁷ , R ⁷ and R ⁸ , R ⁹ and R ¹⁰ , R ¹⁰ and R ¹¹ , R ¹¹ and R ¹³ , R ¹³ and R ¹⁴ are , respectively, in the case of C ₄ -C ₁₀ may form a saturated or unsaturated ring, wherein said ring crosslinked to each other, an oxygen atom, a sulfur atom, a silicon atom, tin atom, germanium atom or the formula -N ( B) — may be interrupted by a group represented by the formula (wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) and may have a substituent.

In the general formula ^{(23), R 3, R} 5 ~R 11, R 13, R 14 is a hydrogen atom, which may have a substituent C ₁ -C ₂₀ hydrocarbon group, optionally having a substituent which may be C ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group which may have a substituent amino group, which may have a substituent a silyl group which may have a substituent alkylthio group (-SY ^1, in the formula, Y ¹ is a good C ₁ -C ₂₀ alkyl group which may have a substituent.), have a substituent An optionally substituted arylthio group (—SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), an optionally substituted alkylsulfonyl A group (—SO ₂ Y ³ , wherein Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group), an optionally substituted arylsulfonyl group (—SO 2 ₂ Y ⁴ , where Y ⁴ represents an optionally substituted C ₆ -C ₂₀ aryl group), a hydroxyl group or a halogen atom. R ³ , R ^{5 to} R ¹¹ , R ¹³ and R ¹⁴ are independent of each other and may be the same or different. R ³ and R ⁵ , R ⁵ and R ⁶ , R ⁶ and R ⁷ , R ⁷ and R ⁸ , R ⁹ and R ¹⁰ , R ¹⁰ and R ¹¹ , R ¹¹ and R ¹³ , R ¹³ and R ¹⁴ are , respectively, in the case of C ₄ -C ₁₀ may form a saturated or unsaturated ring, wherein said ring crosslinked to each other, an oxygen atom, a sulfur atom, a silicon atom, tin atom, germanium atom or the formula -N ( B) — may be interrupted by a group represented by the formula (wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) and may have a substituent.

(Tenth embodiment)
The tenth embodiment of the present invention is a method for producing a biaryl compound represented by the following general formula (25) by reacting dienein represented by the following general formula (24) in the presence of a ruthenium or molybdenum catalyst. It is.

In the general formula (24), R ^{1 to} R ³ , R ^{6 to} R ¹¹ , and R ^{14 to} R ¹⁶ are a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group which may have a substituent, and a substituent. which may have a C ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, substituted An optionally substituted silyl group, an optionally substituted alkylthio group (-SY ¹ , wherein Y ¹ represents an optionally substituted C ₁ -C ₂₀ alkyl group), also an optionally substituted arylthio group (-SY ^2, in the formula, Y ² is a good C ₆ -C ₂₀ aryl group which may have a substituent.), have a substituent which may alkylsulfonyl group (-SO ₂ Y ^3, in the formula, Y ³ represents a good C ₁ -C ₂₀ alkyl group which may have a substituent.), an arylsulfonyl optionally having substituent group (-SO ₂ Y ⁴ In the formula, Y ⁴ is a good C ₆ -C ₂₀ aryl group which may have a substituent.), A hydroxyl group or a halogen atom. R ^{1 to} R ³ , R ^{6 to} R ¹¹ , and R ^{14 to} R ¹⁶ are independent of each other and may be the same or different. Also, R ¹ and R ² , R ⁶ and R ⁷ , R ⁷ and R ⁸ , R ⁹ and R ¹⁰ , R ¹⁰ and R ¹¹ , R ¹⁵ and R ¹⁶ are cross-linked with each other to form C _{4 to} C _10. A saturated ring or an unsaturated ring may be formed. In the case of the ring, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom, or a group represented by the formula —N (B) — (wherein B Is a hydrogen atom or a C ₁ -C ₁₀ hydrocarbon group.) And may have a substituent. X is an oxygen atom, a sulfur atom or a nitrogen atom which may have a substituent.

In the above general formula (25), R ³ , R ^{6 to} R ¹¹ and R ¹⁴ may have a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group which may have a substituent, or a substituent. good C ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, a silyl group, which may have a substituent , which may have a substituent alkylthio group (-SY ^1, wherein, Y ¹ is. showing a good C ₁ -C ₂₀ alkyl group which may have a substituent), have a substituent An optionally substituted arylthio group (—SY ² , wherein Y ² represents an optionally substituted C _{6 to} C ₂₀ aryl group), an optionally substituted alkylsulfonyl group ( —SO ₂ Y ³ , wherein Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group), and optionally substituted arylsulfonyl group (—SO ₂ Y ^4, in the formula, Y ⁴ May have a substituent represents an C ₆ -C ₂₀ aryl group.), A hydroxyl group or a halogen atom. R ^{1 to} R ³ , R ^{6 to} R ¹¹ , and R ^{14 to} R ¹⁶ are independent of each other and may be the same or different. Also, R ¹ and R ² , R ⁶ and R ⁷ , R ⁷ and R ⁸ , R ⁹ and R ¹⁰ , R ¹⁰ and R ¹¹ , R ¹⁵ and R ¹⁶ are cross-linked with each other to form C _{4 to} C _10. A saturated ring or an unsaturated ring may be formed. In the case of the ring, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom, or a group represented by the formula —N (B) — (wherein B Is a hydrogen atom or a C ₁ -C ₁₀ hydrocarbon group.) And may have a substituent. X is an oxygen atom, a sulfur atom or a nitrogen atom which may have a substituent.

(Eleventh embodiment)
In the eleventh embodiment of the present invention, an enyne represented by the following general formula (26) is reacted in the presence of a ruthenium or molybdenum catalyst to generate a cyclic compound represented by the following general formula (27). And a biaryl compound represented by the following general formula (28) is further produced by thermal decomposition or reaction in the presence of an acid or a base.

In the general formula (26), R ^{1 to} R ¹⁶ are a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group that may have a substituent, or a C _{1 to} C that may have a substituent. ₂₀ alkoxy group, optionally substituted C ₆ -C ₂₀ aryloxy group, optionally substituted amino group, optionally substituted silyl group, substituted An optionally substituted alkylthio group (—SY ¹ , wherein Y ¹ represents an optionally substituted C ₁ -C ₂₀ alkyl group), an optionally substituted arylthio group (—SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), an optionally substituted alkylsulfonyl group (—SO ₂ Y ³ In the formula, Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group.), An optionally substituted arylsulfonyl group (—SO ₂ Y ⁴ , Y ⁴ is a substituted group Have shown a good C ₆ -C ₂₀ aryl group.), A hydroxyl group or a halogen atoms. R ^{1 to} R ¹⁶ are independent of each other and may be the same or different. R ¹ and R ² , R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ⁶ and R ⁸ , R ¹⁰ and R ¹¹ , R ¹¹ and R ¹² , R ¹² and R ¹³ , R ¹³ and R ¹⁴ , R ¹⁵ and R ¹⁶ may be bridged with each other to form a C _{4 to} C ₁₀ saturated or unsaturated ring, and in the case of the ring, an oxygen atom, a sulfur atom, a silicon atom , Tin atom, germanium atom or a group represented by the formula —N (B) — (wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group), and substituted It may have a group.

In the general formula (27), R ^{3 to} R ¹⁴ are a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group which may have a substituent, or a C _{1 to} C which may have a substituent. ₂₀ alkoxy group, optionally substituted C ₆ -C ₂₀ aryloxy group, optionally substituted amino group, optionally substituted silyl group, substituted An optionally substituted alkylthio group (—SY ¹ , wherein Y ¹ represents an optionally substituted C ₁ -C ₂₀ alkyl group), an optionally substituted arylthio group (—SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), an optionally substituted alkylsulfonyl group (—SO ₂ Y ³ In the formula, Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group.), An optionally substituted arylsulfonyl group (—SO ₂ Y ⁴ , Y ⁴ is a substituted group Have shown a good C ₆ -C ₂₀ aryl group.), A hydroxyl group or a halogen atoms. R ^{3 to} R ¹⁴ are independent of each other and may be the same or different. R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ⁶ and R ⁸ , R ¹⁰ and R ¹¹ , R ¹¹ and R ¹² , R ¹² and R ¹³ , R ¹³ and R ¹⁴ are Each may be bridged with each other to form a C _{4 to} C ₁₀ saturated or unsaturated ring, in the case of said rings, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom or a formula —N (B ) — (Wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) and may have a substituent.

In the above general formula (28), R ^{3 to} R ⁶ , R ⁸ and R ^{10 to} R ¹⁴ have a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group which may have a substituent, and a substituent. which may be C ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, which may have a substituent a silyl group which may have a substituent alkylthio group (-SY ^1, in the formula, Y ¹ is a good C ₁ -C ₂₀ alkyl group which may have a substituent.), a substituent have good arylthio group (-SY ^2, in the formula, Y ² is a good C ₆ -C ₂₀ aryl group which may have a substituent.), an alkyl which may have a substituent A sulfonyl group (—SO ₂ Y ³ , wherein Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group), an optionally substituted arylsulfonyl group (— SO ₂ Y ⁴ , where Y ⁴ represents an optionally substituted C ₆ -C ₂₀ aryl group.), A hydroxyl group or a halogen atom. R ^{3 to} R ⁶ , R ⁸ and R ^{10 to} R ¹⁴ are independent of each other and may be the same or different. R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ⁶ and R ⁸ , R ¹⁰ and R ¹¹ , R ¹¹ and R ¹² , R ¹² and R ¹³ , R ¹³ and R ¹⁴ are Each may be bridged with each other to form a C _{4 to} C ₁₀ saturated or unsaturated ring, in the case of said rings, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom or a formula —N (B ) — (Wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) and may have a substituent.

(Twelfth embodiment)
In the twelfth embodiment of the present invention, a biaryl compound represented by the following general formula (30) is produced by reacting a dienein represented by the following general formula (29) in the presence of a ruthenium or molybdenum catalyst. It is a method to do.

In the general formula (29), R ^{1 to} R ⁶ and R ^{11 to} R ^{16 each} have a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group that may have a substituent, or a substituent. which may C ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, which may have a substituent silyl group, which may have a substituent alkylthio group (-SY ^1, in the formula, Y ¹ is a good C ₁ -C ₂₀ alkyl group which may have a substituent.), a substituent An optionally substituted arylthio group (—SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), an optionally substituted alkylsulfonyl group (-SO ₂ Y ^3, in the formula, Y ³ represents a good C ₁ -C ₂₀ alkyl group which may have a substituent.), which may have a substituent arylsulfonyl group (-SO ₂ Y ⁴ , where Y ⁴ represents an optionally substituted C ₆ -C ₂₀ aryl group), a hydroxyl group or a halogen atom. R ^{1 to} R ⁶ and R ^{11 to} R ¹⁶ are independent of each other and may be the same or different. R ¹ and R ² , R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ¹¹ and R ¹² , R ¹² and R ¹³ , R ¹³ and R ¹⁴ , R ¹⁵ and R ¹⁶ are Each may be bridged with each other to form a C _{4 to} C ₁₀ saturated or unsaturated ring, in the case of said rings, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom or a formula —N (B ) — (Wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) and may have a substituent. X is an oxygen atom, a sulfur atom or a nitrogen atom which may have a substituent.

In the general formula (30), R ^{3 to} R ⁶ and R ^{11 to} R ^{14 each} have a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group that may have a substituent, or a substituent. which may C ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, which may have a substituent silyl group, which may have a substituent alkylthio group (-SY ^1, in the formula, Y ¹ is a good C ₁ -C ₂₀ alkyl group which may have a substituent.), a substituent An optionally substituted arylthio group (—SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), an optionally substituted alkylsulfonyl group (-SO ₂ Y ^3, in the formula, Y ³ represents a good C ₁ -C ₂₀ alkyl group which may have a substituent.), which may have a substituent arylsulfonyl group (-SO ₂ Y ⁴ , where Y ⁴ represents an optionally substituted C ₆ -C ₂₀ aryl group), a hydroxyl group or a halogen atom. R ^{3 to} R ⁶ and R ^{11 to} R ¹⁴ are independent of each other and may be the same or different. R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ¹¹ and R ¹² , R ¹² and R ¹³ , R ¹³ and R ¹⁴ , R ¹⁵ and R ¹⁶ are cross-linked with each other. C _{4 to} C ₁₀ may form a saturated or unsaturated ring, and in the case of the ring, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom, or a group represented by the formula —N (B) — (Wherein B is a hydrogen atom or a C ₁ -C ₁₀ hydrocarbon group) and may have a substituent. X is an oxygen atom, a sulfur atom or a nitrogen atom which may have a substituent.

  Next, a method for producing the biaryl compound according to Embodiments 1 to 12 will be described.

(First manufacturing condition)
First, the raw materials represented by the general formulas (1), (6), (11), (16), (21), and (26) are reacted in the presence of a ruthenium catalyst or a molybdenum catalyst, After generating the cyclic compound represented by the general formula (2), (7), (12), (17), (22), (27), (2), (7), (12), ( 17), (22), and (27) are desorbed and expressed by general formulas (3), (8), (13), (18), (23), and (28), respectively. Biaryl compounds can be obtained.

  In this production method, the ruthenium catalyst or the molybdenum catalyst may be used as it is, or may be supported on a substance that does not dissolve in the solvent used for the reaction, such as carbon, silica, or alumina. In such a reaction, the amount of the ruthenium catalyst or molybdenum catalyst used is usually 0.00001 mol times or more, usually 1 mol times or less, preferably 0.2 mol times or less, relative to the raw material. In addition, the acid or base used for the elimination reaction may be used as it is, or may be supported on a substance that does not dissolve in the solvent used for the reaction, such as carbon, silica, or alumina. In such a reaction, the amount used is usually 0.00001 mol times or more, usually 100 mol times or less, preferably 0.2 mol times or less, relative to the raw material.

This reaction is usually performed in an organic solvent. Examples of organic solvents include aprotic polar solvents such as N-methylpyrrolidone, N, N-dimethylformamide, dimethyl sulfoxide, acetonitrile, diethyl ether, diisopropyl ether, diethylene glycol dimethyl ether, 1,4-dioxane, Examples thereof include ether solvents such as tetrahydrofuran, aromatic hydrocarbons such as benzene, toluene and xylene, aliphatic hydrocarbons such as hexane and heptane, and halogen-containing solvents such as dichloromethane, chloroform and dichloroethane.
The solvents are used alone or in combination of two or more, and the amount used is usually 1 to 2000 times, preferably 5 to 500 times, the raw material.

  The above reaction may be performed in air or in an atmosphere of nitrogen or ethylene gas. The gas pressure is usually about 1 to 500 atmospheres, preferably about 1 to 5 atmospheres.

  The above reaction is preferably performed in a temperature range of −78 ° C. or higher and 200 ° C. or lower, more preferably 0 ° C. or higher and 150 ° C. or lower, and further preferably 20 ° C. or higher and 100 ° C. or lower.

  The reaction time for the above reaction is not particularly limited, but is preferably 1 minute to 24 hours, more preferably 10 minutes to 12 hours.

  And after completion | finish of this reaction, the produced | generated biaryl compound represented by the said General formula (3), (8), (13), (18), (23), (28) is obtained by distilling a solvent off, for example. Can be removed from the reaction mass. In addition, the obtained biaryl compound can be further purified by applying a means such as recrystallization as necessary.

  In this reaction, the raw material, the ruthenium catalyst or molybdenum catalyst, and the solvent can be added in any order.

(Second manufacturing condition)
Next, the raw materials represented by the general formulas (4), (9), (14), (19), (24), and (29) are reacted in the presence of a ruthenium catalyst or a molybdenum catalyst. Production methods for obtaining biaryl compounds represented by the general formulas (5), (10), (15), (20), (25), and (30) will be described.

  In this production method, the ruthenium catalyst or the molybdenum catalyst may be used as it is, or may be supported on a substance that does not dissolve in the solvent used for the reaction, such as carbon, silica, or alumina. In such a reaction, the amount of the ruthenium catalyst or molybdenum catalyst used is usually 0.00001 mol times or more, usually 1 mol times or less, preferably 0.2 mol times or less, relative to the raw material.

This reaction is usually performed in an organic solvent. Examples of organic solvents include aprotic polar solvents such as N-methylpyrrolidone, N, N-dimethylformamide, dimethyl sulfoxide, acetonitrile, diethyl ether, diisopropyl ether, diethylene glycol dimethyl ether, 1,4-dioxane, Examples thereof include ether solvents such as tetrahydrofuran, aromatic hydrocarbons such as benzene, toluene and xylene, aliphatic hydrocarbons such as hexane and heptane, and halogen-containing solvents such as dichloromethane, chloroform and dichloroethane.
The solvents are used alone or in combination of two or more, and the amount used is usually 1 to 2000 times, preferably 5 to 500 times, the raw material.

  In addition, this reaction may be performed under air or in an atmosphere of nitrogen or ethylene gas. The gas pressure is usually about 1 to 500 atmospheres, preferably about 1 to 5 atmospheres.

  The reaction temperature range of this reaction is preferably −78 ° C. or higher and 200 ° C. or lower, more preferably 0 ° C. or higher and 150 ° C. or lower, and further preferably 20 ° C. or higher and 100 ° C. or lower.

  The reaction time for this reaction is not particularly limited, but is preferably 1 minute to 24 hours, more preferably 10 minutes to 12 hours.

  After the completion of this reaction, the produced biaryl compounds (5), (10), (15), (20), (25), and (30) are removed from the reaction mass by, for example, distilling off the solvent. Can do. In addition, the obtained biaryl compound can be further purified by applying a means such as recrystallization as necessary.

  In this reaction, the raw material, the ruthenium catalyst, and the solvent can be added in any order.

  Hereinafter, specific confirmation was performed as confirmation of the effects of the present invention. This will be specifically described below.

Example 1
1- (5-fluoro-2-((6- (1-hydroxybut-3-enyl) benzo [d] [1,3] dioxol-5-yl) ethynyl) phenyl) but-3- A suspension of en-1-ol (59.0 mg, 0.155 mmol) in toluene (27 mL) was heated to 50 ° C. for 10 minutes, and then cooled to room temperature. Grubbs catalyst second generation (10.2 mg, 0.012 mmol) was added to the reaction vessel and stirred at 80 degrees for 2 hours. Then, the reaction liquid was cooled to room temperature, paratoluenesulfonic acid (2.4 mg, 0.014 mmol) was added, and it stirred for 1 hour. The solvent was distilled off from the reaction solution under reduced pressure, and the resulting residue was purified using silica gel chromatography (hexane / dichloromethane = 1/1) to obtain the desired 5- (6-fluoronaphthalen-1-yl) naphtho. [2,3-d] [1,3] dioxole (41.2 mg, 84%) was obtained. The melting point, NMR data, and HRMS data were as follows.

mp 215−218 ° C; ¹ H
NMR (CDCl ₃ ) ・ 5.95 (s, 2H), 6.59 (s, 1H),
7.06 (ddd, J = 9.2, 8.2, 2.5 Hz, 1H), 7.21 (s, 1H), 7.31 (dd, J =
7.0, 1.2 Hz, 1H), 7.37 (dd, J = 9.5, 5.8 Hz, 1H), 7.41−7.44 (m, 2H), 7.53 (dd, J = 9.8, 2.8 Hz, 1H), 7.59 (t, J
= 7.7 Hz, 1H), 7.76 (d, J = 8.3 Hz, 1H), 7.86 (d, J = 8.2 Hz,
1H); ¹³ C NMR (CDCl ₃ ) ... 101.02, 102.65,
104.04, 111.03 (d, J = 20.1 Hz), 116.28 (d, J = 25.1 Hz), 123.94,
126.37, 126.57, 126.89 (d, J = 2.0 Hz), 127.05, 127.20 (d, J =
5.0 Hz), 129.12 (d, J = 9.0 Hz), 129.77, 129.82, 130.70, 134.46 (d, J
= 9.1 Hz), 137.24, 139.00, 147.49, 147.84, 160.57 (d, J = 245.5 Hz);
HRMS (FAB) calcd for C ₂₁ H ₁₃ FO ₂ (M ⁺ )
316.0900, found 316.0912.

The present invention has industrial applicability as a method for producing a biaryl compound.

Claims (12)

The enyne represented by the following general formula (1) is reacted in the presence of a ruthenium or molybdenum catalyst to generate a cyclic compound represented by the following general formula (2), and further, thermal decomposition or in the presence of an acid or a base To produce a biaryl compound represented by the following general formula (3).
(In the above formula, R ^{1 to} R ¹⁶ are a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group which may have a substituent, a C _{1 to} C ₂₀ alkoxy group which may have a substituent, C ₆ -C ₂₀ aryloxy group which may have a substituent, amino group which may have a substituent, silyl group which may have a substituent, may have a substituent alkylthio group (-SY ^1, in the formula, Y ¹ is a good C ₁ -C ₂₀ alkyl group which may have a substituent.), which may have a substituent arylthio group (-SY ² In the formula, Y ² represents an optionally substituted C _{6 to} C ₂₀ aryl group.), An optionally substituted alkylsulfonyl group (—SO ₂ Y ³ , Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group.), An optionally substituted arylsulfonyl group (—SO ₂ Y ⁴ , wherein Y ⁴ represents a substituted group) Even if you have a group . Showing a have C ₆ -C ₂₀ aryl group), a hydroxyl group or a halogen atom. Further, R ¹ to R ¹⁶ are each independently of one another, may be the same or different. Also, R ¹ and R ^2, R ³ and R ^4, R ⁴ and R ^6, R ⁶ and R ^7, R ⁷ and R ^8, R ⁹ and R ^10, R ¹⁰ and R ^12, R ¹² and R ^13, R ¹³ and R ¹⁴ R ¹⁵ and R ¹⁶ may be bridged with each other to form a C _{4 to} C ₁₀ saturated ring or an unsaturated ring, and in the case of the ring, an oxygen atom, a sulfur atom, a silicon atom, tin May be interrupted by an atom, a germanium atom or a group represented by —N (B) — (where B is a hydrogen atom or a C ₁ -C ₁₀ hydrocarbon group) and has a substituent. May be.)
(In the formula, R ^{3 to} R ¹⁴ are each a hydrogen atom, an optionally substituted C _{1 to} C ₂₀ hydrocarbon group, an optionally substituted C _{1 to} C ₂₀ alkoxy group, or a substituted group. C ₆ -C ₂₀ aryloxy group optionally having a group, amino group optionally having a substituent, silyl group optionally having a substituent, and optionally having a substituent An alkylthio group (—SY ¹ , wherein Y ¹ represents an optionally substituted C ₁ -C ₂₀ alkyl group), an optionally substituted arylthio group (—SY ² , In the formula, Y ² represents an optionally substituted C _{6 to} C ₂₀ aryl group.), An optionally substituted alkylsulfonyl group (—SO ₂ Y ³ , wherein Y ³ represents an C ₁ -C ₂₀ alkyl group which may have a substituent.), which may have a substituent arylsulfonyl group (-SO ₂ Y ^4,: in the formula, Y ⁴ is a substituent C which may have _{6 to} C ₂₀ aryl group), a hydroxyl group or a halogen atom, and R ^{3 to} R ¹⁴ may be the same or different from each other, and R ³ and R ⁴ , R ⁴ And R ⁶ , R ⁶ and R ⁷ , R ⁷ and R ⁸ , R ⁹ and R ¹⁰ , R ¹⁰ and R ¹² , R ¹² and R ¹³ , and R ¹³ and R ¹⁴ are cross-linked with each other to form C ₄ -C ₁₀ may form a saturated or unsaturated ring, and in the case of the ring, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom or a group represented by -N (B)-(where B is a hydrogen atom or a C ₁ -C ₁₀ hydrocarbon group.) may be interrupted by, and may have a substituent.)
(In the formula, R ³ , R ⁴ , R ^{6 to} R ¹⁰ , R ^{12 to} R ^{14 each} have a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group that may have a substituent, or a substituent. which may be C ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group which may have a substituent amino group, which may have a substituent a silyl group which may have a substituent alkylthio group (-SY ^1, in the formula, Y ¹ is a good C ₁ -C ₂₀ alkyl group which may have a substituent.), have a substituent An optionally substituted arylthio group (—SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), an optionally substituted alkylsulfonyl A group (—SO ₂ Y ³ , wherein Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group), an optionally substituted arylsulfonyl group (—SO 2 ₂ Y ^4,: in the formula, Y ⁴ is a substituted The. Indicating an even better C ₆ -C ₂₀ aryl group which may have), a hydroxyl group or a halogen atom. Further, R ³ to R ¹⁴ are each independently of one another, may be the same or different. Further, R ³ and R ⁴ , R ⁴ and R ⁶ , R ⁶ and R ⁷ , R ⁷ and R ⁸ , R ⁹ and R ¹⁰ , R ¹⁰ and R ¹² , R ¹² and R ¹³ , and R ¹³ and R ¹⁴ are respectively in the case of C ₄ -C ₁₀ may form a saturated or unsaturated ring, wherein said ring crosslinked to each other, an oxygen atom, a sulfur atom, a silicon atom, tin atom, germanium atom or -N (B) (It may be interrupted by a group represented by — (wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) and may have a substituent.) A method for producing a biaryl compound represented by the general formula (5) by reacting a dienein represented by the following general formula (4) in the presence of a ruthenium or molybdenum catalyst.
(In the formula, R ^{1 to} R ⁴ , R ^{7 to} R ¹⁰ , R ^{13 to} R ¹⁶ have a hydrogen atom, an optionally substituted C _{1 to} C ₂₀ hydrocarbon group, and a substituent. which may be C ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group which may have a substituent amino group, which may have a substituent a silyl group which may have a substituent alkylthio group (-SY ^1, in the formula, Y ¹ is a good C ₁ -C ₂₀ alkyl group which may have a substituent.), have a substituent An optionally substituted arylthio group (—SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), an optionally substituted alkylsulfonyl A group (—SO ₂ Y ³ , wherein Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group), an optionally substituted arylsulfonyl group (—SO 2 ₂ Y ⁴ , where Y ⁴ is a substitution A C ₆ -C ₂₀ aryl group optionally having a group), a hydroxyl group, or a halogen atom, and R ^{1 to} R ⁴ , R ^{7 to} R ¹⁰ , and R ^{13 to} R ¹⁶ are respectively R ¹ and R ² , R ³ and R ⁴ , R ⁷ and R ⁸ , R ⁹ and R ¹⁰ , R ¹³ and R ¹⁴ , R ¹⁵ and R ¹⁶ may each be bridged with each other to form a C _{4 to} C ₁₀ saturated ring or unsaturated ring, and in the case of the ring, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom, or a formula − It may be interrupted by a group represented by N (B)-(wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) and may have a substituent. X is an oxygen atom, a sulfur atom or a nitrogen atom which may have a substituent.)
(In the formula, R ³ , R ⁴ , R ^{7 to} R ¹⁰ , R ¹³ , R ¹⁴ have a hydrogen atom, an optionally substituted C _{1 to} C ₂₀ hydrocarbon group, and a substituent. which may be C ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group which may have a substituent amino group, which may have a substituent a silyl group which may have a substituent alkylthio group (-SY ^1, in the formula, Y ¹ is a good C ₁ -C ₂₀ alkyl group which may have a substituent.), have a substituent An optionally substituted arylthio group (—SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), an optionally substituted alkylsulfonyl A group (—SO ₂ Y ³ , wherein Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group), an optionally substituted arylsulfonyl group (—SO 2 ₂ Y ⁴ , where Y ⁴ is a substitution A C ₆ -C ₂₀ aryl group optionally having a group), a hydroxyl group, or a halogen atom, and R ³ , R ⁴ , R ⁷ -R ¹⁰ , R ¹³ , R ¹⁴ are independently of one another, may be the same or different. the R ³ and R ^4, R ⁷ and R ^8, R ⁹ and R ^10, R ¹³ and R ¹⁴ are each, C ₄ ~ crosslinked to each other A C ₁₀ saturated ring or an unsaturated ring may be formed, and in the case of the ring, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom, or a group represented by the formula —N (B) — , B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) and may have a substituent, and X is an oxygen atom, a sulfur atom or a substituent. It is a nitrogen atom that may have a group.) The enyne represented by the following general formula (6) is reacted in the presence of a ruthenium or molybdenum catalyst to generate a cyclic compound represented by the following general formula (7), followed by thermal decomposition, or in the presence of an acid or base. To produce a biaryl compound represented by the following general formula (8).
(In the formula, R ^{1 to} R ¹⁶ are a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group which may have a substituent, a C _{1 to} C ₂₀ alkoxy group which may have a substituent, a substituted group. C ₆ -C ₂₀ aryloxy group which may have a group, amino group which may have a substituent, silyl group which may have a substituent, and may have a substituent An alkylthio group (—SY ¹ , wherein Y ¹ represents an optionally substituted C ₁ -C ₂₀ alkyl group), an optionally substituted arylthio group (—SY ² , In the formula, Y ² represents an optionally substituted C _{6 to} C ₂₀ aryl group.), An optionally substituted alkylsulfonyl group (—SO ₂ Y ³ , wherein Y ³ represents an C ₁ -C ₂₀ alkyl group which may have a substituent.), which may have a substituent arylsulfonyl group (-SO ₂ Y ^4,: in the formula, Y ⁴ is a substituent C which may have _{6 to} C ₂₀ aryl group), a hydroxyl group, or a halogen atom, and R ^{1 to} R ¹⁶ may be the same or different from each other, and R ¹ and R ² , R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁷ , R ⁷ and R ⁸ , R ⁹ and R ¹¹ , R ¹¹ and R ¹² , R ¹² and R ¹³ , R ¹³ and R ¹⁴ , R ¹⁵ and R ¹⁶ may be bridged with each other to form a C _{4 to} C ₁₀ saturated ring or unsaturated ring, and in the case of the ring, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, germanium It may be interrupted by an atom or a group represented by the formula —N (B) — (wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) and has a substituent. May be.)
(Wherein R ^{3 to} R ¹⁴ are a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group which may have a substituent, a C _{1 to} C ₂₀ alkoxy group which may have a substituent, a substituent. the -C ₂₀ C ₆ which may have an aryloxy group, an optionally substituted amino group, which may have a substituent silyl group, which may have a substituent alkylthio group (-SY ^1, in the formula, Y ¹ is a good C ₁ -C ₂₀ alkyl group which may have a substituent.), also an optionally substituted arylthio group (-SY ^2, wherein in, Y ² is represents an C ₆ -C ₂₀ aryl group which may have a substituent.), which may have a substituent alkylsulfonyl group (-SO ₂ Y ^3, wherein, Y ³ shows a good C ₁ -C ₂₀ alkyl group which may have a substituent.), which may have a substituent arylsulfonyl group (-SO ₂ Y ^4,: in the formula, Y ⁴ is a substituent C ₆ which may have -C ₂₀ aryl group), a hydroxyl group, or a halogen atom, and R ^{3 to} R ¹⁴ may be the same or different from each other, and R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁷ , R ⁷ and R ⁸ , R ⁹ and R ¹¹ , R ¹¹ and R ¹² , R ¹² and R ¹³ , R ¹³ and R ¹⁴ are cross-linked with each other to form C ₄ -C ₁₀ may form a saturated or unsaturated ring, if the ring is an oxygen atom, a sulfur atom, a silicon atom, tin atom, germanium atom or the formula -N (B) - group represented by ( In the formula, B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) and may be interrupted and may have a substituent.
(Where R ^{3 to} R ⁵
, R ^{7 to} R ⁹ and R ^{11 to} R ¹⁴ are a hydrogen atom, an optionally substituted C _{1 to} C ₂₀ hydrocarbon group, and an optionally substituted C _{1 to} C ₂₀ alkoxy. Group, a C _{6 to} C ₂₀ aryloxy group which may have a substituent, an amino group which may have a substituent, a silyl group which may have a substituent, and a substituent. An optionally substituted alkylthio group (—SY ¹ , wherein Y ¹ represents an optionally substituted C ₁ -C ₂₀ alkyl group), an optionally substituted arylthio group (— SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group.), An optionally substituted alkylsulfonyl group (—SO ₂ Y ³ , formula In the formula, Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group.), An optionally substituted arylsulfonyl group (—SO ₂ Y ⁴ , wherein Y ⁴ Has a substituent There shows a C ₆ -C ₂₀ aryl group.), A hydroxyl group, or a halogen atom. R ^{3 to} R ⁵ , R ^{7 to} R ⁹ , and R ^{11 to} R ¹⁴ are independent of each other and may be the same or different. R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁷ , R ⁷ and R ⁸ , R ⁹ and R ¹¹ , R ¹¹ and R ¹² , R ¹² and R ¹³ , R ¹³ and R ¹⁴ are , respectively, in the case of C ₄ -C ₁₀ may form a saturated or unsaturated ring, wherein said ring crosslinked to each other, an oxygen atom, a sulfur atom, a silicon atom, tin atom, germanium atom or the formula -N ( B) — may be interrupted by a group represented by the formula (wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) and may have a substituent. ) A process for producing a biaryl compound represented by the general formula (10), wherein the dienein represented by the following general formula (9) is reacted in the presence of a ruthenium or molybdenum catalyst.
(In the formula, R ^{1 to} R ⁵ , R ⁸ , R ⁹ , R ^{12 to} R ¹⁶ have a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group which may have a substituent, or a substituent. which may be C ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group which may have a substituent amino group, which may have a substituent a silyl group which may have a substituent alkylthio group (-SY ^1, in the formula, Y ¹ is a good C ₁ -C ₂₀ alkyl group which may have a substituent.), have a substituent An optionally substituted arylthio group (—SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), an optionally substituted alkylsulfonyl A group (—SO ₂ Y ³ , wherein Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group), an optionally substituted arylsulfonyl group (—SO 2 ₂ Y ^4,: in the formula, Y ⁴ is a substituted Even when the have shown a good C ₆ -C ₂₀ aryl group.), A hydroxyl group, or a halogen atom. ^{Further, R 1 ~R 5, R 8} , R 9, R 12 ~R 16 are each respectively They may be the same or different, and R ¹ and R ² , R ³ and R ⁴ , R ⁴ and R ⁵ , R ¹² and R ¹³ , R ¹³ and R ¹⁴ , R ¹⁵ and R ¹⁶ May each be bridged with each other to form a C _{4 to} C ₁₀ saturated or unsaturated ring, in the case of said rings, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom or a formula —N (B) -. groups (. wherein, B is a hydrogen atom or a C ₁ -C ₁₀ hydrocarbon group) represented by which may be interrupted by, and may have a substituent group or , X is an oxygen atom, a sulfur atom, or a nitrogen atom which may have a substituent.
(In the formula, R ^{3 to} R ⁵ , R ⁸ , R ⁹ , R ^{12 to} R ¹⁴ have a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group that may have a substituent, or a substituent. which may be C ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group which may have a substituent amino group, which may have a substituent a silyl group which may have a substituent alkylthio group (-SY ^1, in the formula, Y ¹ is a good C ₁ -C ₂₀ alkyl group which may have a substituent.), have a substituent An optionally substituted arylthio group (—SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), an optionally substituted alkylsulfonyl A group (—SO ₂ Y ³ , wherein Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group), an optionally substituted arylsulfonyl group (—SO 2 ₂ Y ^4,: in the formula, Y ⁴ is a substituted The have shown even better C ₆ -C ₂₀ aryl group.), A hydroxyl group, or a halogen atom. In ^{addition, R 3 ~R 5, R 8} , R 9, R 12 ~R 14 are each respectively They may be the same or different, and R ³ and R ⁴ , R ⁴ and R ⁵ , R ¹² and R ¹³ , R ¹³ and R ¹⁴ may be cross-linked with each other to form C ₄ -C _{10 A} saturated ring or an unsaturated ring may be formed, and in the case of the ring, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom, or a group represented by the formula —N (B) — (wherein B is a hydrogen atom or a C ₁ -C ₁₀ hydrocarbon group.) may be interrupted by, and may have a substituent. Further, X represents an oxygen atom, a sulfur atom, or a substituted It is a nitrogen atom that may have a group.) The enyne represented by the following general formula (11) is reacted in the presence of a ruthenium or molybdenum catalyst to generate a cyclic compound represented by the general formula (12). A method for producing a biaryl compound represented by the following general formula (13), which is reacted in the presence of a base.
(In the formula, R ^{1 to} R ¹⁶ are a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group which may have a substituent, a C _{1 to} C ₂₀ alkoxy group which may have a substituent, a substituted group. C ₆ -C ₂₀ aryloxy group which may have a group, amino group which may have a substituent, silyl group which may have a substituent, and may have a substituent An alkylthio group (—SY ¹ , wherein Y ¹ represents an optionally substituted C ₁ -C ₂₀ alkyl group), an optionally substituted arylthio group (—SY ² , In the formula, Y ² represents an optionally substituted C _{6 to} C ₂₀ aryl group.), An optionally substituted alkylsulfonyl group (—SO ₂ Y ³ , wherein Y ³ represents an C ₁ -C ₂₀ alkyl group which may have a substituent.), which may have a substituent arylsulfonyl group (-SO ₂ Y ^4,: in the formula, Y ⁴ is a substituent C which may have _{6 to} C ₂₀ aryl group), a hydroxyl group, or a halogen atom, and R ^{1 to} R ¹⁶ may be the same or different from each other, and R ¹ and R ² , R ³ and R ⁵ , R ⁵ and R ⁶ , R ⁶ and R ⁷ , R ⁷ and R ⁸ , R ⁹ and R ¹⁰ , R ¹⁰ and R ¹¹ , R ¹¹ and R ¹³ , R ¹³ and R ¹⁴ , R ¹⁵ and R ¹⁶ may be bridged with each other to form a C _{4 to} C ₁₀ saturated ring or unsaturated ring, and in the case of the ring, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, germanium It may be interrupted by an atom or a group represented by the formula —N (B) — (wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) and has a substituent. May be.)
(In the formula, R ^{3 to} R ¹⁴ are each a hydrogen atom, an optionally substituted C _{1 to} C ₂₀ hydrocarbon group, an optionally substituted C _{1 to} C ₂₀ alkoxy group, or a substituted group. C ₆ -C ₂₀ aryloxy group which may have a group, amino group which may have a substituent, silyl group which may have a substituent, and may have a substituent An alkylthio group (—SY ¹ , wherein Y ¹ represents an optionally substituted C ₁ -C ₂₀ alkyl group), an optionally substituted arylthio group (—SY ² , In the formula, Y ² represents an optionally substituted C _{6 to} C ₂₀ aryl group.), An optionally substituted alkylsulfonyl group (—SO ₂ Y ³ , wherein Y ³ represents an C ₁ -C ₂₀ alkyl group which may have a substituent.), which may have a substituent arylsulfonyl group (-SO ₂ Y ^4,: in the formula, Y ⁴ is a substituent C which may have _{6 to} C ₂₀ aryl group), a hydroxyl group, or a halogen atom, and R ^{3 to} R ¹⁴ may be the same or different from each other, and R ³ and R ⁵ , R ⁵ and R ⁶ , R ⁶ and R ⁷ , R ⁷ and R ⁸ , R ⁹ and R ¹⁰ , R ¹⁰ and R ¹¹ , R ¹¹ and R ¹³ , R ¹³ and R ¹⁴ are cross-linked with each other. May form a C _{4 to} C ₁₀ saturated ring or an unsaturated ring, and in the case of the ring, it is represented by an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom, or a formula —N (B) —. (In the formula, B may be a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) and may have a substituent.)
(In the formula, R ³ , R ^{5 to} R ¹¹ , R ¹³ and R ¹⁴ may have a hydrogen atom, a C ₁ -C ₂₀ hydrocarbon group which may have a substituent, or a substituent. C ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, a silyl group which may have a substituent, An optionally substituted alkylthio group (-SY ¹ , wherein Y ¹ represents an optionally substituted C ₁ -C ₂₀ alkyl group), and has a substituent; which may arylthio group (. -SY ^2, wherein, Y ² is showing a good C ₆ -C ₂₀ aryl group which may have a substituent), which may have a substituent, an alkylsulfonyl group (- SO ₂ Y ³ , wherein Y ³ represents a C _{1 to} C ₂₀ alkyl group which may have a substituent, and an arylsulfonyl group (—SO ₂ Y ⁴ which may have a substituent). in the formula, Y ⁴ is a substituent And shows also good C ₆ -C ₂₀ aryl group optionally.), A hydroxyl group, or a halogen atom. In ^{addition, R 3, R 5 ~R 11} , R 13, R 14 are each independently of one another, identical R ³ and R ⁵ , R ⁵ and R ⁶ , R ⁶ and R ⁷ , R ⁷ and R ⁸ , R ⁹ and R ¹⁰ , R ¹⁰ and R ¹¹ , R ¹¹ and R ¹³ , R ¹³ and R ¹⁴ may be bridged with each other to form a C _{4 to} C ₁₀ saturated ring or unsaturated ring, and in the case of the ring, an oxygen atom, a sulfur atom, a silicon atom, tin An atom, a germanium atom, or a group represented by the formula —N (B) — (wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group), (You may have it.) A method for producing a biaryl compound represented by the following general formula (15) by reacting dienein represented by the following general formula (14) in the presence of a ruthenium or molybdenum catalyst.
(In the formula, R ^{1 to} R ³ , R ^{6 to} R ¹¹ , R ^{14 to} R ¹⁶ have a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group which may have a substituent, and a substituent. which may C ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, which may have a substituent silyl group, which may have a substituent alkylthio group (-SY ^1, in the formula, Y ¹ is a good C ₁ -C ₂₀ alkyl group which may have a substituent.), a substituent An optionally substituted arylthio group (—SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), an optionally substituted alkylsulfonyl group (-SO ₂ Y ^3, in the formula, Y ³ represents a good C ₁ -C ₂₀ alkyl group which may have a substituent.), which may have a substituent arylsulfonyl group (-SO ₂ Y ^4,: in the formula, Y ⁴ is a substituent A represents an C ₆ -C ₂₀ aryl group optionally.), A hydroxyl group or a halogen atom. ^{Further, R 1 ~R 3, R 6} ~R 11, R 14 ~R 16 are each independently of one another R ¹ and R ² , R ⁶ and R ⁷ , R ⁷ and R ⁸ , R ⁹ and R ¹⁰ , R ¹⁰ and R ¹¹ , R ¹⁵ and R ¹⁶ are Each may be bridged with each other to form a C _{4 to} C ₁₀ saturated or unsaturated ring, in the case of said rings, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom or a formula —N (B ) — (Wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) and may have a substituent. Is an oxygen atom, a sulfur atom or an optionally substituted nitrogen atom.)
^{(Wherein, R 3, R 6 ~R 11} , R 14 is a hydrogen atom, which may have a substituent C ₁ -C ₂₀ hydrocarbon group which may have a substituent C ₁ -C ₂₀ alkoxy group, optionally substituted C ₆ -C ₂₀ aryloxy group, optionally substituted amino group, optionally substituted silyl group, substituted An optionally substituted alkylthio group (—SY ¹ , wherein Y ¹ represents an optionally substituted C ₁ -C ₂₀ alkyl group), an optionally substituted arylthio group (—SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), an optionally substituted alkylsulfonyl group (—SO ₂ Y ³ In the formula, Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group.), An optionally substituted arylsulfonyl group (—SO ₂ Y ⁴ , Y ⁴ is substituted Also represents an C ₆ -C ₂₀ aryl group.), A hydroxyl group or a halogen atom. In ^{addition, R 3, R 6 ~R 11} , R 14 are each independently of one another, be different even in the same R ⁶ and R ⁷ , R ⁷ and R ⁸ , R ⁹ and R ¹⁰ , R ¹⁰ and R ¹¹ may be bridged with each other to form a C _{4 to} C ₁₀ saturated or unsaturated ring. Well, in the case of the ring, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom or a group represented by the formula —N (B) — (wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon And may have a substituent, and X is an oxygen atom, a sulfur atom or a nitrogen atom which may have a substituent.) The enyne represented by the following general formula (16) is reacted in the presence of a ruthenium or molybdenum catalyst to generate a cyclic compound represented by the following general formula (17), and further, thermal decomposition or in the presence of an acid or a base To produce a biaryl compound represented by the following general formula (18).
(In the formula, R ^{1 to} R ¹⁶ are a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group which may have a substituent, a C _{1 to} C ₂₀ alkoxy group which may have a substituent, a substituted group. C ₆ -C ₂₀ aryloxy group which may have a group, amino group which may have a substituent, silyl group which may have a substituent, and may have a substituent An alkylthio group (—SY ¹ , wherein Y ¹ represents an optionally substituted C ₁ -C ₂₀ alkyl group), an optionally substituted arylthio group (—SY ² , In the formula, Y ² represents an optionally substituted C _{6 to} C ₂₀ aryl group.), An optionally substituted alkylsulfonyl group (—SO ₂ Y ³ , wherein Y ³ represents an C ₁ -C ₂₀ alkyl group which may have a substituent.), which may have a substituent arylsulfonyl group (-SO ₂ Y ^4,: in the formula, Y ⁴ is a substituent C which may have _{6 to} C ₂₀ aryl group), a hydroxyl group or a halogen atom, and R ^{1 to} R ¹⁶ may be the same or different from each other, and R ¹ and R ² may be the same. , R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ⁶ and R ⁸ , R ¹⁰ and R ¹¹ , R ¹¹ and R ¹² , R ¹² and R ¹³ , R ¹³ and R ¹⁴ , R ¹⁵ and R ¹⁶ may be bridged with each other to form a C _{4 to} C ₁₀ saturated ring or an unsaturated ring, and in the case of the ring, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom or the formula -N (B) - group (. wherein, B is a hydrogen atom or a C ₁ -C ₁₀ hydrocarbon group) represented by may be interrupted by, and have a substituent May be good.)
(In the formula, R ^{3 to} R ¹⁴ are each a hydrogen atom, an optionally substituted C _{1 to} C ₂₀ hydrocarbon group, an optionally substituted C _{1 to} C ₂₀ alkoxy group, or a substituted group. C ₆ -C ₂₀ aryloxy group which may have a group, amino group which may have a substituent, silyl group which may have a substituent, and may have a substituent An alkylthio group (—SY ¹ , wherein Y ¹ represents an optionally substituted C ₁ -C ₂₀ alkyl group), an optionally substituted arylthio group (—SY ² , In the formula, Y ² represents an optionally substituted C _{6 to} C ₂₀ aryl group.), An optionally substituted alkylsulfonyl group (—SO ₂ Y ³ , wherein Y ³ represents an C ₁ -C ₂₀ alkyl group which may have a substituent.), which may have a substituent arylsulfonyl group (-SO ₂ Y ^4,: in the formula, Y ⁴ is a substituent C which may have ₆ -C showing a ₂₀ aryl group.), There Oh in a hydroxyl group or a halogen atom. Further, R ³ to R ¹³ are each independently of one another, may be different even in the same. The R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ⁶ and R ⁸ , R ¹⁰ and R ¹¹ , R ¹¹ and R ¹² , R ¹² and R ¹³ , R ¹³ and R ¹⁴ are cross-linked with each other. C _{4 to} C ₁₀ may form a saturated or unsaturated ring, and in the case of the ring, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom, or a group represented by the formula —N (B) — (In the formula, B may be a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group.) And may have a substituent.)
(Wherein R ^{3 to} R ⁶ , R ⁸ and R ^{10 to} R ¹⁴ may have a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group which may have a substituent, or a substituent. C ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, a silyl group which may have a substituent, An optionally substituted alkylthio group (-SY ¹ , wherein Y ¹ represents an optionally substituted C ₁ -C ₂₀ alkyl group), and has a substituent; which may arylthio group (. -SY ^2, wherein, Y ² is showing a good C ₆ -C ₂₀ aryl group which may have a substituent), which may have a substituent, an alkylsulfonyl group (- SO ₂ Y ³ , wherein Y ³ represents a C _{1 to} C ₂₀ alkyl group which may have a substituent, and an arylsulfonyl group (—SO ₂ Y ⁴ which may have a substituent). In the formula, Y ⁴ has a substituent. An optionally substituted C ₆ -C ₂₀ aryl group), a hydroxyl group or a halogen atom, and R ^{3 to} R ⁶ , R ⁸ and R ^{10 to} R ¹⁴ are each independently the same R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ⁶ and R ⁸ , R ¹⁰ and R ¹¹ , R ¹¹ and R ¹² , R ¹² and R ¹³ , R ¹³ and R ¹⁴ may be bridged with each other to form a C _{4 to} C ₁₀ saturated or unsaturated ring, and in the case of the ring, an oxygen atom, a sulfur atom, a silicon atom, a tin atom , A germanium atom or a group represented by the formula —N (B) — (wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) and has a substituent. You may do it.) A method for producing a biaryl compound represented by the following general formula (20) by reacting a dienein represented by the following general formula (19) in the presence of a ruthenium or molybdenum catalyst.
(In the formula, R ^{1 to} R ⁶ and R ^{11 to} R ¹⁶ are each a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group which may have a substituent, or a C ₁ to which may have a substituent. C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, which may have a substituent silyl group, a substituent have alkylthio group (-SY ^1, shown in the formula, Y ¹ is an optionally C ₁ -C ₂₀ alkyl group which may have a substituent.) may arylthio optionally having substituent A group (—SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), an optionally substituted alkylsulfonyl group (—SO ₂ Y ³ , wherein Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group.), An optionally substituted arylsulfonyl group (—SO ₂ Y ⁴ , , Y ⁴ is a substituent Even represents an C ₆ -C ₂₀ aryl group.), A hydroxyl group or a halogen atom.
R ^{1 to} R ⁶ and R ^{11 to} R ¹⁶ are independent of each other and may be the same or different. R ¹ and R ² , R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ¹¹ and R ¹² , R ¹² and R ¹³ , R ¹³ and R ¹⁴ , R ¹⁵ and R ¹⁶ are Each may be bridged with each other to form a C _{4 to} C ₁₀ saturated or unsaturated ring, in the case of said rings, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom or a formula —N (B ) — (Wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) and may have a substituent. X is an oxygen atom; a sulfur atom; or a nitrogen atom that may have a substituent. )
(Wherein R ^{3 to} R ⁶ and R ^{11 to} R ¹⁴ are a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group that may have a substituent, and a C ₁ to C that may have a substituent. C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, which may have a substituent silyl group, a substituent have alkylthio group (-SY ^1, shown in the formula, Y ¹ is an optionally C ₁ -C ₂₀ alkyl group which may have a substituent.) may arylthio optionally having substituent A group (—SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), an optionally substituted alkylsulfonyl group (—SO ₂ Y ³ , wherein Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group.), An optionally substituted arylsulfonyl group (—SO ₂ Y ⁴ , , Y ⁴ is a substituent Represents an C ₆ -C ₂₀ aryl group.), A hydroxyl group or a halogen atom. In ^{addition, R 3 ~R 6, R 11} ~R 14 are each independently of one another, optionally substituted by one or more identical R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ¹¹ and R ¹² , R ¹² and R ¹³ , R ¹³ and R ¹⁴ are each cross-linked to form C ₄ to A C ₁₀ saturated ring or an unsaturated ring may be formed, and in the case of the ring, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom, or a group represented by the formula —N (B) — , B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) and may have a substituent, and X is an oxygen atom; a sulfur atom; (It is a nitrogen atom which may have a substituent.) The enyne represented by the following general formula (21) is reacted in the presence of a ruthenium or molybdenum catalyst to generate a cyclic compound represented by the following general formula (22), and further in the presence of heat decomposition or the presence of an acid or a base. A process for producing a biaryl compound represented by the following general formula (23) by reacting.
(In the formula, R ^{1 to} R ¹⁶ are a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group which may have a substituent, a C _{1 to} C ₂₀ alkoxy group which may have a substituent, a substituted group. C ₆ -C ₂₀ aryloxy group which may have a group, amino group which may have a substituent, silyl group which may have a substituent, and may have a substituent An alkylthio group (—SY ¹ , wherein Y ¹ represents an optionally substituted C ₁ -C ₂₀ alkyl group), an optionally substituted arylthio group (—SY ² , In the formula, Y ² represents an optionally substituted C _{6 to} C ₂₀ aryl group.), An optionally substituted alkylsulfonyl group (—SO ₂ Y ³ , wherein Y ³ represents an C ₁ -C ₂₀ alkyl group which may have a substituent.), which may have a substituent arylsulfonyl group (-SO ₂ Y ^4,: in the formula, Y ⁴ is a substituent C which may have _{6 to} C ₂₀ aryl group), a hydroxyl group or a halogen atom, and R ^{1 to} R ¹⁶ may be the same or different from each other, and R ¹ and R ² , R ³ and R ⁵ , R ⁵ and R ⁶ , R ⁶ and R ⁷ , R ⁷ and R ⁸ , R ⁹ and R ¹⁰ , R ¹⁰ and R ¹¹ , R ¹¹ and R ¹³ , R ¹³ and R ¹⁴ , R ¹⁵ And R ¹⁶ may be bridged with each other to form a C _{4 to} C ₁₀ saturated or unsaturated ring, and in the case of the ring, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom, or It may be interrupted by a group represented by the formula —N (B) — (wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) and may have a substituent. Good.)
(In the formula, R ^{3 to} R ¹⁴ are each a hydrogen atom, an optionally substituted C _{1 to} C ₂₀ hydrocarbon group, an optionally substituted C _{1 to} C ₂₀ alkoxy group, or a substituted group. C ₆ -C ₂₀ aryloxy group which may have a group, amino group which may have a substituent, silyl group which may have a substituent, and may have a substituent An alkylthio group (—SY ¹ , wherein Y ¹ represents an optionally substituted C ₁ -C ₂₀ alkyl group), an optionally substituted arylthio group (—SY ² , In the formula, Y ² represents an optionally substituted C _{6 to} C ₂₀ aryl group.), An optionally substituted alkylsulfonyl group (—SO ₂ Y ³ , wherein Y ³ represents an C ₁ -C ₂₀ alkyl group which may have a substituent.), which may have a substituent arylsulfonyl group (-SO ₂ Y ^4,: in the formula, Y ⁴ is a substituent C which may have _{6 to} C ₂₀ aryl group), a hydroxyl group or a halogen atom, and R ^{3 to} R ¹⁴ may be the same or different from each other, R ³ and R ⁵ , R ⁵ and R ⁶ , R ⁶ and R ⁷ , R ⁷ and R ⁸ , R ⁹ and R ¹⁰ , R ¹⁰ and R ¹¹ , R ¹¹ and R ¹³ , R ¹³ and R ¹⁴ are cross-linked with each other to form C ₄ -C ₁₀ may form a saturated or unsaturated ring, if the ring is an oxygen atom, a sulfur atom, a silicon atom, tin atom, germanium atom or the formula -N (B) - group represented by ( In the formula, B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) and may be interrupted and may have a substituent.
(Wherein R ³ , R ^{5 to} R ¹¹ , R ¹³ and R ¹⁴ are hydrogen atoms, C _{1 to} C ₂₀ hydrocarbon groups optionally having substituents, and C optionally having substituents. ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, a silyl group which may have a substituent group, a substituted alkylthio group which may have a group (-SY ^1, in the formula, Y ¹ is a good C ₁ -C ₂₀ alkyl group which may have a substituent.), which may have a substituent A good arylthio group (—SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), an optionally substituted alkylsulfonyl group (—SO 2; ₂ Y ³ , wherein Y ³ represents an optionally substituted C _{1 to} C ₂₀ alkyl group.), An optionally substituted arylsulfonyl group (—SO ₂ Y ⁴ , : in the formula, Y ⁴ is have a substituent Even though showing a good C ₆ -C ₂₀ aryl group.), A hydroxyl group or a halogen atom. In ^{addition, R 3, R 5 ~R 11} , R 13, R 14 are each independently of one another, be the same R ³ and R ⁵ , R ⁵ and R ⁶ , R ⁶ and R ⁷ , R ⁷ and R ⁸ , R ⁹ and R ¹⁰ , R ¹⁰ and R ¹¹ , R ¹¹ and R ¹³ , R ¹³ and R ¹⁴ may be bridged with each other to form a C _{4 to} C ₁₀ saturated or unsaturated ring, and in the case of the ring, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, germanium It may be interrupted by an atom or a group represented by the formula —N (B) — (wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) and has a substituent. May be.) A process for producing a biaryl compound represented by the following general formula (25) by reacting dienein represented by the following general formula (24) in the presence of a ruthenium or molybdenum catalyst.
(In the formula, R ^{1 to} R ³ , R ^{6 to} R ¹¹ , R ^{14 to} R ¹⁶ have a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group which may have a substituent, and a substituent. which may C ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, which may have a substituent silyl group, which may have a substituent alkylthio group (-SY ^1, in the formula, Y ¹ is a good C ₁ -C ₂₀ alkyl group which may have a substituent.), a substituent An optionally substituted arylthio group (—SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), an optionally substituted alkylsulfonyl group (-SO ₂ Y ^3, in the formula, Y ³ represents a good C ₁ -C ₂₀ alkyl group which may have a substituent.), which may have a substituent arylsulfonyl group (-SO ₂ Y ^4,: in the formula, Y ⁴ is a substituent A represents an C ₆ -C ₂₀ aryl group optionally.), A hydroxyl group or a halogen atom. ^{Further, R 1 ~R 3, R 6} ~R 11, R 14 ~R 16 each independently of one another, R ¹ and R ² , R ⁶ and R ⁷ , R ⁷ and R ⁸ , R ⁹ and R ¹⁰ , R ¹⁰ and R ¹¹ , R ¹⁵ and R ¹⁶ may be the same or different. Each may be bridged with each other to form a C _{4 to} C ₁₀ saturated or unsaturated ring, in the case of said rings, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom or a formula —N (B ) — (Wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) and may have a substituent. Is an oxygen atom, a sulfur atom or a nitrogen atom which may have a substituent.)
^{(Wherein, R 3, R 6 ~R 11} , R 14 is a hydrogen atom, which may have a substituent C ₁ -C ₂₀ hydrocarbon group which may have a substituent C ₁ -C ₂₀ alkoxy group, optionally substituted C ₆ -C ₂₀ aryloxy group, optionally substituted amino group, optionally substituted silyl group, substituted An optionally substituted alkylthio group (—SY ¹ , wherein Y ¹ represents an optionally substituted C ₁ -C ₂₀ alkyl group), an optionally substituted arylthio group (—SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), an optionally substituted alkylsulfonyl group (—SO ₂ Y ³ In the formula, Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group.), An optionally substituted arylsulfonyl group (—SO ₂ Y ⁴ , Y ⁴ is substituted Also represents an C ₆ -C ₂₀ aryl group.), A hydroxyl group or a halogen atom. ^{Further, R 1 ~R 3, R 6} ~R 11, R 14 ~R 16 each independently of one another, be the same R ¹ and R ² , R ⁶ and R ⁷ , R ⁷ and R ⁸ , R ⁹ and R ¹⁰ , R ¹⁰ and R ¹¹ , R ¹⁵ and R ¹⁶ are cross-linked with each other. C _{4 to} C ₁₀ saturated ring or unsaturated ring may be formed, and in the case of the ring, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom, or a formula —N (B) — (Wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) and may have a substituent, and X is an oxygen atom , A sulfur atom or a nitrogen atom which may have a substituent.) An enyne represented by the following general formula (26) is reacted in the presence of a ruthenium or molybdenum catalyst to generate a cyclic compound represented by the following general formula (27), and further, thermal decomposition or in the presence of an acid or a base To produce a biaryl compound represented by the following general formula (28).
(In the formula, R ^{1 to} R ¹⁶ are a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group which may have a substituent, a C _{1 to} C ₂₀ alkoxy group which may have a substituent, a substituted group. C ₆ -C ₂₀ aryloxy group which may have a group, amino group which may have a substituent, silyl group which may have a substituent, and may have a substituent An alkylthio group (—SY ¹ , wherein Y ¹ represents an optionally substituted C ₁ -C ₂₀ alkyl group), an optionally substituted arylthio group (—SY ² , In the formula, Y ² represents an optionally substituted C _{6 to} C ₂₀ aryl group.), An optionally substituted alkylsulfonyl group (—SO ₂ Y ³ , wherein Y ³ represents an C ₁ -C ₂₀ alkyl group which may have a substituent.), which may have a substituent arylsulfonyl group (-SO ₂ Y ^4,: in the formula, Y ⁴ is a substituent C which may have _{6 to} C ₂₀ aryl group), a hydroxyl group or a halogen atom, and R ^{1 to} R ¹⁶ may be the same or different from each other, R ¹ and R ² , R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ⁶ and R ⁸ , R ¹⁰ and R ¹¹ , R ¹¹ and R ¹² , R ¹² and R ¹³ , R ¹³ and R ¹⁴ , R ¹⁵ And R ¹⁶ may be bridged with each other to form a C _{4 to} C ₁₀ saturated or unsaturated ring, and in the case of the ring, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom, or It may be interrupted by a group represented by the formula —N (B) — (wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) and may have a substituent. Good.)
(In the formula, R ^{3 to} R ¹⁴ are each a hydrogen atom, an optionally substituted C _{1 to} C ₂₀ hydrocarbon group, an optionally substituted C _{1 to} C ₂₀ alkoxy group, or a substituted group. C ₆ -C ₂₀ aryloxy group which may have a group, amino group which may have a substituent, silyl group which may have a substituent, and may have a substituent An alkylthio group (—SY ¹ , wherein Y ¹ represents an optionally substituted C ₁ -C ₂₀ alkyl group), an optionally substituted arylthio group (—SY ² , In the formula, Y ² represents an optionally substituted C _{6 to} C ₂₀ aryl group.), An optionally substituted alkylsulfonyl group (—SO ₂ Y ³ , wherein Y ³ represents an C ₁ -C ₂₀ alkyl group which may have a substituent.), which may have a substituent arylsulfonyl group (-SO ₂ Y ^4,: in the formula, Y ⁴ is a substituent C which may have _{6 to} C ₂₀ aryl group), a hydroxyl group or a halogen atom, and R ^{3 to} R ¹⁴ may be the same or different from each other, R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ⁶ and R ⁸ , R ¹⁰ and R ¹¹ , R ¹¹ and R ¹² , R ¹² and R ¹³ , R ¹³ and R ¹⁴ are cross-linked with each other to form C ₄ -C ₁₀ may form a saturated or unsaturated ring, if the ring is an oxygen atom, a sulfur atom, a silicon atom, tin atom, germanium atom or the formula -N (B) - group represented by ( In the formula, B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) and may be interrupted and may have a substituent.
(In the formula, R ^{3 to} R ⁶ , R ⁸ and R ^{10 to} R ¹⁴ are hydrogen atoms, C ₁ -C ₂₀ hydrocarbon groups optionally having substituents, C optionally having substituents. ₁ -C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, a silyl group which may have a substituent group, a substituted alkylthio group which may have a group (-SY ^1, in the formula, Y ¹ is a good C ₁ -C ₂₀ alkyl group which may have a substituent.), which may have a substituent A good arylthio group (—SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), an optionally substituted alkylsulfonyl group (—SO 2; ₂ Y ³ , wherein Y ³ represents an optionally substituted C _{1 to} C ₂₀ alkyl group.), An optionally substituted arylsulfonyl group (—SO ₂ Y ⁴ , In the formula, Y ⁴ has a substituent. An optionally substituted C ₆ -C ₂₀ aryl group), a hydroxyl group or a halogen atom, and R ^{3 to} R ⁶ , R ⁸ , and R ^{10 to} R ¹⁴ are independent of each other and are the same. R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ⁶ and R ⁸ , R ¹⁰ and R ¹¹ , R ¹¹ and R ¹² , R ¹² and R ¹³ , R ¹³ and R ¹⁴ may be bridged with each other to form a C _{4 to} C ₁₀ saturated or unsaturated ring, and in the case of the ring, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, germanium It may be interrupted by an atom or a group represented by the formula —N (B) — (wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) and has a substituent. May be.) A method for producing a biaryl compound represented by the following general formula (30) by reacting a dienein represented by the following general formula (29) in the presence of a ruthenium or molybdenum catalyst.
(In the formula, R ^{1 to} R ⁶ and R ^{11 to} R ¹⁶ are each a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group which may have a substituent, or a C ₁ to which may have a substituent. C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, which may have a substituent silyl group, a substituent have alkylthio group (-SY ^1, shown in the formula, Y ¹ is an optionally C ₁ -C ₂₀ alkyl group which may have a substituent.) may arylthio optionally having substituent A group (—SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), an optionally substituted alkylsulfonyl group (—SO ₂ Y ³ , wherein Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group.), An optionally substituted arylsulfonyl group (—SO ₂ Y ⁴ , , Y ⁴ is a substituent Represents an C ₆ -C ₂₀ aryl group.), A hydroxyl group or a halogen atom. ^{Further, R 1 ~R 6, R 11} ~R 16 each independently of one another, be different even in the same R ¹ and R ² , R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ¹¹ and R ¹² , R ¹² and R ¹³ , R ¹³ and R ¹⁴ , R ¹⁵ and R ¹⁶ May each be bridged with each other to form a C _{4 to} C ₁₀ saturated or unsaturated ring, in the case of said rings, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom or a formula —N (B) -. groups (. wherein, B is a hydrogen atom or a C ₁ -C ₁₀ hydrocarbon group) represented by which may be interrupted by, and may have a substituent group or , X is an oxygen atom, a sulfur atom or a nitrogen atom which may have a substituent.)
(Wherein R ^{3 to} R ⁶ and R ^{11 to} R ¹⁴ are a hydrogen atom, a C _{1 to} C ₂₀ hydrocarbon group that may have a substituent, and a C ₁ to C that may have a substituent. C ₂₀ alkoxy group which may have a substituent C ₆ -C ₂₀ aryloxy group, an optionally substituted amino group, which may have a substituent silyl group, a substituent have alkylthio group (-SY ^1, shown in the formula, Y ¹ is an optionally C ₁ -C ₂₀ alkyl group which may have a substituent.) may arylthio optionally having substituent A group (—SY ² , wherein Y ² represents an optionally substituted C ₆ -C ₂₀ aryl group), an optionally substituted alkylsulfonyl group (—SO ₂ Y ³ , wherein Y ³ represents an optionally substituted C ₁ -C ₂₀ alkyl group.), An optionally substituted arylsulfonyl group (—SO ₂ Y ⁴ , , Y ⁴ is a substituent Represents an C ₆ -C ₂₀ aryl group.), A hydroxyl group or a halogen atom. In ^{addition, R 3 ~R 6, R 11} ~R 14 each independently of one another, be different even in the same R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ¹¹ and R ¹² , R ¹² and R ¹³ , R ¹³ and R ¹⁴ , R ¹⁵ and R ¹⁶ are cross-linked with each other. C _{4 to} C ₁₀ saturated ring or unsaturated ring may be formed, and in the case of the ring, an oxygen atom, a sulfur atom, a silicon atom, a tin atom, a germanium atom, or a formula —N (B) — (Wherein B is a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group) and may have a substituent, and X is an oxygen atom , A sulfur atom or a nitrogen atom which may have a substituent.)