KR102037409B1 - Noble selenium ring compounds and manufacturing method for the same - Google Patents

Abstract

Provided is a method for synthesizing a selenium ring compound, which comprises the steps of: causing, under a rhodium catalytic reaction, a reactant 1, an aromatic ring compound in which at least two nitrogens and selenium constitute a ring element, to be reacted with a reactant 2 having a double or more bond; and synthesizing a selenium ring compound by adding an element having a double or more bond to two or more nitrogen positions according to the reaction, wherein the reactant 1 is AA, and the reactant 2 is a compound containing any one of an alkane bond, an alkene bond, a nitrile bond, and a diene bond. Each of the R^1 and R^2 may be any one selected from the group consisting of hydrogen, a halogen group, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 1 to 10 carbon atoms, an alkynyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 12 carbon atoms, and an alkyloxy group having 1 to 10 carbon atoms, and the R^1 and R^2 may be connected to each other to form a fused ring. According to the present invention, it is possible to synthesize the selenium ring compound of a novel structure according to a kind of a substituent.

Description

Novel selenium ring compounds and manufacturing method for the same

The present invention relates to a novel selenium ring compound and a method for preparing the same, and more particularly, to an aromatic ring compound in which two or more nitrogen and selenium form a ring element in the presence of a rhodium catalyst, and a compound having at least a double bond or more rings The present invention relates to a novel selenium ring compound and a method for producing the same.

Selenium ring compounds are widely used as pharmaceuticals and electronic materials. Among selenium ring compounds, selenadiazole refers to an aromatic compound consisting of a five-membered ring composed of one selenium atom, two nitrogen atoms, and two carbon atoms, and 1,2,3-, 1,2,4 depending on the position of the nitrogen atom. -, 1,3,4-, 1,2,5-selenadiazole (Selenadiazole) (see Formula 1).

[Equation 1]

Among them, 1,2,3-selenadiazole is known to form biradical intermediates or zwitterion intermediates as nitrogen is released by light and heat (see Equation 2).

[Equation 2]

Synthetic methods in which alkene or alkoxyl groups are added from these intermediates have been reported in various literatures. For example, a paper reported by Sonoda Group in 2000 and 2002 (a) Socoda N, J. Organomet. Chem . 2000 , 611, 488. b) Socoda N, J. Organomet. Chem . (2002 , 67, 1520) reported the synthesis of dihydroselenophene by the reaction of cyclic selenadiazole with olefins.

(C) Arsenyan P. Tetrahedron Lett , reported by the Arsenyan Group in 2002. (2002 , 43, 4817) reported an example of synthesizing selenofene with substituents at positions 2 and 5 by reaction of selenadiazole with alkane. As such, 1,2,3-selenadiazole is widely used for the synthesis of heterocyclic compounds containing selenium.

1,2,3-oxadiazole, 1,2,3-triazole, 1,2,3-thiadiazole with similar structure to 1,2,3-selenadiazole are ring-chain totalization Through the formation of the following diazoketone, diazoimine, diazothion and then to the metal catalyst through the denitrification reaction with a metal catalyst to form (see Equation 3). The metal carbene thus formed may be used in the synthesis of various heterocyclic compounds through cyclization with various reactants.

[Equation 3]

On the other hand, a rhodium oxabinilcarbene intermediate may be formed through denitrification of a diazoketone, which is a ring opening form of oxadiazole, with a rhodium catalyst.

(D) Davies, HML Tetrahedron 1988 , 44, 3343. e) Davies, HML Org. Synth . 1992 , 90, 93.) reported the synthesis of furan by the cyclization reaction of oxavinylcarbene intermediate with alkane. In addition, in 1990, Pad and group reported the synthesis of furan by intramolecular cyclization of α-diazoketone containing alkane in tetrahydron letter in 1990 (f) Padwa, A. Tetrahedron 1990 , 31, 6835.)

In addition, triazole is known to equilibrate triazole foam and diazoimine foam through ring-chain totalization, and pyrrole through cyclization reaction with alkane via azavinylcarbene intermediate through reaction with metal catalyst. Can be synthesized.

In 2009, the Murakami Group reported an example of pyrrole synthesis using a nickel catalyst, and in 2011, an example of pyrrole synthesis using a rhodium catalyst was reported from the Geborgian group ((g) Murakami, M. Chem Commun . 2009 , 1470. h) Gevorgyan, V. Org. Lett . 2011, 13, 3746.)

Also, in 2016, the Giadianzol and Professor Pilho Lee's group equilibrated with diazothiol through ring-chain atomization, and form rhodium cyvinylcarbene by denitrification with rhodium catalyst. We report the synthesis of thiophene and isothiazol by cyclization with alkane, nitrile and olepin (i) Gevorgyan, V. Org. Lett . 2011, 13, 3746., j) Lee, P. H. Org. Lett . K, Lee, P. H. 2016 , 18, 5050 . Org. Lett . 2016, 18, 5038.)

Among these selenium ring compounds, selenophene, which is a pentagonal ring, is used as a basic structure of various compounds.

Since selenophene has pharmacological activity, it is included in the skeletal structure of the molecule which has a better effect on breast cancer, hepatocellular carcinoma and cervical cancer than zephytinib, which is used as an anticancer agent. . It is also included in the skeletal structure of OLEDs and solar cells because of its optical properties.

The general method of synthesizing selenopene is to add alkane and selenium and heat it. In another way, in 2007, the Jenny group reported the production of selenophene, which contains alkyne-containing selenoids through hydrosele- tion, and then synthesizes selenophene by reacting with an electrophile with an electrotrophil. l) Zeni, GJ Org. Chem . 2007 , 72, 6726.)

However, no example has been reported of effectively synthesizing selenophene using a catalyst.

The present invention provides a novel selenium ring compound having pharmacological activity and optical activity and a preparation method thereof.

In order to solve the above problems, the present invention comprises the steps of reacting reactant 1, which is an aromatic ring compound in which two or more nitrogen and selenium constitute a ring element, and reactant 2 having at least a double bond or more under a rhodium catalytic reaction; And synthesizing a selenium ring compound by adding an element having at least two double bonds as a ring element at the two or more nitrogen positions according to the reaction.

이고, The reactant 1 is

ego,

The reactant 2 provides a method of synthesizing a selenium ring compound, wherein the compound includes any one of an alkane, an alkene, nitrile, and a diene bond.

R ¹ and R ² are each a hydrogen, a halogen group, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 1 to 10 carbon atoms, an alkynyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, A substituted or unsubstituted heteroaryl group having 5 to 12 carbon atoms and alkyloxy group having 1 to 10 carbon atoms, any one selected from the group consisting of, R ¹ and R ² may be connected to each other to form a fused ring R ¹ , R ² is hydrogen, a halogen group, an alkyl group of 1 to 10 carbon atoms, an alkenyl group of 1 to 10 carbon atoms, an alkynyl group of 1 to 10 carbon atoms, a substituted or unsubstituted aryl group of 6 to 12 carbon atoms, substituted or unsubstituted, respectively It is carbon atoms and one selected from the group consisting of a heteroaryl group of from 5 to 12, and an alkyloxy group having 1 to 10 carbon atoms one, wherein R ¹ and R ² are connected to each other can be formed of a fused ring )

In one embodiment of the present invention, the selenium ring compound synthesis method, according to the reaction formula represented by the following formula 4.

[Equation 4]

(In Formula 4, R ³ is a halogen group, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 1 to 10 carbon atoms, an alkynyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, substituted or substituted. Unsubstituted heteroaryl group having 5 to 12 carbon atoms, M is a metal catalyst containing rhodium, wherein in Formula 4, R ³ is hydrogen, a halogen group, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 1 to 10 carbon atoms, An alkynyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 12 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms , Alkyl group having 7 to 15 carbon atoms, M is a metal catalyst containing rhodium)

In one embodiment of the present invention, the method for synthesizing a thin selenium ring compound proceeds according to a reaction formula represented by the following Formula 5.

[Equation 5]

'

In Formula 5, R ⁴ represents a hydrogen, a halogen group, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 1 to 10 carbon atoms, an alkynyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, and a substitution. Or a substituted or unsubstituted heteroaryl group of 5 to 12 carbon atoms, haloalkyl group of 1 to 10 carbon atoms, alkoxy group of 1 to 10 carbon atoms, alkylphenyl group of 7 to 15 carbon atoms, M is a metal catalyst including rhodium )

In one embodiment of the present invention, the selenium ring compound synthesis method, according to the reaction formula represented by the following formula 6.

[Equation 6]

In Formula 6, R ⁵ represents a hydrogen, a halogen group, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 1 to 10 carbon atoms, an alkynyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, and a substitution. Or a substituted or unsubstituted heteroaryl group having 5 to 12 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, alcohol having 1 to 10 carbon atoms, alkylphenyl having 7 to 15 carbon atoms, and M is a metal catalyst including rhodium)

In one embodiment of the present invention, the selenium ring compound synthesis method, according to the reaction formula represented by the following formula 7.

[Equation 7]

In Formula 7, R ⁶ represents a hydrogen, a halogen group, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 1 to 10 carbon atoms, an alkynyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, and a substitution. Or unsubstituted heteroaryl groups of 5 to 12 carbon atoms, haloalkyl groups of 1 to 10 carbon atoms, alkoxy group alcohols of 1 to 10 carbon atoms, alkylphenyl groups of 7 to 15 carbon atoms, ketone compound groups of 2 to 10 carbon atoms, and carbon atoms of 2 to 10 Any one of 10 carbonyl compound groups, M being a metal catalyst comprising rhodium)

The present invention provides a novel selenium ring compound synthesized by the above-described method as a selenium ring compound, and having any one of the following structural formulas.

The present invention provides a novel selenium ring compound synthesized by the above-described method as a selenium ring compound, and having any one of the following structural formulas.

The present invention provides a novel selenium ring compound synthesized by the above-described method as a selenium ring compound, and having any one of the following structural formulas.

The present invention provides a novel selenium ring compound synthesized by the above-described method as a selenium ring compound, and having any one of the following structural formulas.

According to the invention, selenadiazole is denitrified under a rhodium catalyst to form a metal carbene, and the compound having asymmetrically rich bonds (bonds above the double bond) from the metal carbene is replaced by the nitrogen position. Thereby, the selenium ring compound of the novel structure according to the kind of substituent can be synthesize | combined.

Hereinafter, the present invention will be described in detail.

At this time, if there is no other definition in the technical terms and scientific terms used, it has a meaning commonly understood by those of ordinary skill in the art. In addition, repeated description of the same technical configuration and operation as in the prior art will be omitted.

The present invention can form a novel selenium ring compound by forming a metal carbene as an intermediate with a rhodium catalyst and then reacting with a compound having a functional group asymmetrically enriched in imputation in order to solve the above problems.

In the method of synthesizing a selenium ring compound according to an embodiment of the present invention, reactant 1, which is an aromatic ring compound in which two or more nitrogens and selenium form a ring element, and reactant 2 having at least a double bond or more bonds under a rhodium-catalyzed reaction Making a step; And

In accordance with the reaction comprises the step of adding an element having a bond of at least two double bonds to the two or more nitrogen positions as a ring element to synthesize a selenium ring compound,

이고, The reactant 1 is

ego,

The reactant 2 is a compound containing any one of alkane, alkene, nitrile, and diene bond.

In the formula, R ¹ and R ² are each a hydrogen, a halogen group, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 1 to 10 carbon atoms, an alkynyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl having 6 to 12 carbon atoms, respectively. Group, a substituted or unsubstituted heteroaryl group having 5 to 12 carbon atoms and alkyloxy group having 1 to 10 carbon atoms, any one selected from the group consisting of R ¹ and R ² may be connected to each other to form a fused ring.

In this specification, "substitution" is defined as the substitution of hydrogen for an element or compound except hydrogen in place of hydrogen.

In other words, the present invention particularly relates to the removal of nitrogen from reactant 1 under a rhodium catalyst to form metal carbene, and unstable metal carbene intermediates with electron-rich functional groups (e.g., alkane, alkenes, nitriles, dienes) This reaction is to synthesize a ring compound.

In the present invention, the compound reacting with the metal carbene includes at least one of alkane, olefin, diene, nitrile, and the embodiments of the present invention are summarized below based on the following four schemes.

[Equation 4]

In Formula 4, R ³ is hydrogen, a halogen group, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 1 to 10 carbon atoms, an alkynyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, and a substitution. A substituted or unsubstituted heteroaryl group having 5 to 12 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alcohol group having 1 to 10 carbon atoms, and an alkylphenyl group having 7 to 15 carbon atoms, and M is a metal catalyst including rhodium )

[Equation 5]

In Formula 5, R ⁴ represents a hydrogen, a halogen group, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 1 to 10 carbon atoms, an alkynyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, and a substitution. A substituted or unsubstituted heteroaryl group having 5 to 12 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alcoholcock group having 1 to 10 carbon atoms, and an alkylphenyl group having 7 to 15 carbon atoms, and M is a metal catalyst including rhodium being)

In Equation 5, R ⁴ was continuously added, and then a single bond of the cyclic compound was dehydrogenated to form a double bond through an oxidation process.

[Equation 6]

In Formula 6, R ⁵ represents a hydrogen, a halogen group, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 1 to 10 carbon atoms, an alkynyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, and a substitution. A substituted or unsubstituted heteroaryl group having 5 to 12 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alcoholcock group having 1 to 10 carbon atoms, and an alkylphenyl group having 7 to 15 carbon atoms, and M is a metal including rhodium Catalyst)

Equation 6 was also dehydrogenation after the addition of dienes, the single bond of the cyclic compound was changed to a double bond.

[Equation 7]

In Formula 7, R ⁶ represents a hydrogen, a halogen group, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 1 to 10 carbon atoms, an alkynyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, and a substitution. Or a substituted or unsubstituted C5-12 heteroaryl group, C1-10 haloalkyl group, C1-10 alcoholcock, C7-15 alkylphenyl group, C2-10 ketone compound group, C2-12 Any one of 10 carbonyl compound groups, M being a metal catalyst comprising rhodium)

1.Synthesis according to Equation 4

An example of the following selenium ring compound synthesized according to the above Formula 4 will be described.

Preparation of 2,3,5-Triphenylselenophene

4,5-diphenyl-1,2,3-selenadiazole (57.04 mg, 0.2 mmol), phenylacetylene (0.026 mL, 0.24 mmol), [Rh (COD) Cl] ₂ (2.0 mg, 0.004 mmol), DPEPhos in DCE solvent (5.4 mg, 0.01 mmol) is added and reacted at 130 ° C. for 30 minutes. After completion of the reaction, the solvent is removed using an evaporator. The column (Ether: Haxane = 1: 40) was obtained to obtain a desired compound, 2,3,5-triphenylselenophene (63.2 mg, 88%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.60-7.58 (m, 3H), 7.40-7.36 (m, 2H), 7.33-7.21 (m, 11H).

Preparation of 2,3-Diphenyl-5- ( p -tolyl) selenophene

4,5-diphenyl-1,2,3-selenadiazole (57.04 mg, 0.2 mmol), 4-ethynyltoluene (0.03 mL, 0.24 mmol), [Rh (COD) Cl] ₂ (2.0 mg, 0.004 mmol) in DCE solvent , DPEPhos (5.4 mg, 0.01 mmol) was added, followed by reaction at 130 ° C. for 30 minutes. After completion of the reaction, the solvent is removed using an evaporator. The column (Haxane) was carried out to obtain a desired compound, 2,3-diphenyl-5- ( p -tolyl) selenophene (63.5 mg, 85%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.54 (s, 1H), 7.48 (d, J = 8.1, 2H), 7.33-7.21 (m, 10H), 7.19 (d, J = 7.8, 2H), 2.37 (s, 3 H).

Preparation of 5- (4-Pentylphenyl) -2,3-diphenylselenophene

4,5-diphenyl-1,2,3-selenadiazole (57.04 mg, 0.2 mmol) 1-ethynyl-4-pentylbenzene (0.047 mL, 0.24 mmol), [Rh (COD) Cl] ₂ (2.0 mg, 0.004 mmol) and DPEPhos (5.4 mg, 0.01 mmol) are added, followed by reaction at 130 ° C. for 30 minutes. After completion of the reaction, the solvent is removed using an evaporator. The column (Ethyl acetate: Haxane = 1: 100) was obtained to obtain 5- (4-pentylphenyl) -2,3-diphenyl-selenophene (71.3 mg, 83%) as a desired compound. ¹ H NMR (400 MHz, CDCl ₃ ) d 7.54 (s, 1H), 7.49 (d, J = 8.1, 2H), 7.32-7.18 (m, 12H), 2.62 (t, J = 7.7, 2H), 1.68 -1.60 (m, 2H), 1.36-1.32 (m, 4H), 0.90 (t, J = 6.9, 3H).

Preparation of 5- (2-Methoxyphenyl) -2,3-diphenylselenophene

4,5-diphenyl-1,2,3-selenadiazole (57.04 mg, 0.2 mmol), 1-ethynyl-2-methoxybenzene (0.031 mL, 0.24 mmol), [Rh (COD) Cl] ₂ (2.0 mg) in DCE solvent , 0.004 mmol) and DPEPhos (5.4 mg, 0.01 mmol) were added and then reacted at 130 ° C. for 30 minutes. After completion of the reaction, the solvent is removed using an evaporator. The column (Ethyl acetate: Haxane = 1: 50) was obtained to obtain 5- (2-methoxyphenyl) -2,3-diphenyl-selenophene (67.0 mg, 86%) as a desired compound. ¹ H NMR (400 MHz, CDCl ₃ ) d 7.80 (s, 1H), 7.76-7.73 (m, 1H), 7.34-7.18 (m, 11H), 7.05-7.00 (m, 2H), 3.98 (s, 3H ).

Preparation of 5- (3-Methoxyphenyl) -2,3-diphenylselenophene

4,5-diphenyl-1,2,3-selenadiazole (57.04 mg, 0.2 mmol), 1-ethynyl-3-methoxybenzene (0.03 mL, 0.24 mmol), [Rh (COD) Cl] ₂ (2.0 mg) in DCE solvent , 0.004 mmol) and DPEPhos (5.4 mg, 0.01 mmol) were added and then reacted at 130 ° C. for 30 minutes. After completion of the reaction, the solvent is removed using an evaporator. The column (Ethyl acetate: Haxane = 1: 50) was carried out to obtain 5- (3-methoxyphenyl) -2,3-diphenylselenophene (71.6 mg, 92%) as a desired compound. ¹ H NMR (400 MHz, CDCl ₃ ) d 7.58 (s, 1H), 7.32-7.23 (m, 11H), 7.18 (d, J = 7.7, 1H), 7.12 (t, J = 2.0, 1H), 6.86 (dd, J = 2.2, 8.2, 1H), 3.86 (s, 3H).

Preparation of 5- (4-Methoxyphenyl) -2,3-diphenylselenophene

4,5-diphenyl-1,2,3-selenadiazole (57.04 mg, 0.2 mmol), 1-ethynyl-4-methoxybenzene (0.03 mL, 0.24 mmol), [Rh (COD) Cl] ₂ (2.0 mg) in DCE solvent , 0.004 mmol) and DPEPhos (5.4 mg, 0.01 mmol) were added and then reacted at 130 ° C. for 30 minutes. After completion of the reaction, the solvent is removed using an evaporator. The column (Ether: Haxane = 1: 40) was carried out to obtain 5- (4-methoxyphenyl) -2,3-diphenylselenophene (54.5 mg, 70%) as a desired compound. ¹ H NMR (400 MHz, CD ₂ Cl ₂ ) d 7.53 (dt, J = 9.7, 2.6, 2H), 7.49 (s, 1H), 7.32-7.22 (m, 10H), 6.93 (dt, J = 9.8, 2.6, 2H), 3.83 (s, 3H).

Preparation of 4- (4,5-Diphenylselenophen-2-yl) aniline

4,5-diphenyl-1,2,3-selenadiazole (57.04 mg, 0.2 mmol), 4-ethynylaniline (28.1 mg, 0.24 mmol), [Rh (COD) Cl] ₂ (2.0 mg, 0.004 mmol) in DCE solvent , DPEPhos (5.4 mg, 0.01 mmol) was added, followed by reaction at 130 ° C. for 30 minutes. After completion of the reaction, the solvent is removed using an evaporator. The column (Ethyl acetate: Haxane = 1: 30) was obtained to obtain 4- (4,5-diphenylselenophen-2-yl) aniline (65.1 mg, 87%) as a desired compound.

¹ H NMR (400 MHz, CD ₂ Cl ₂ ) d 7.34 (s, 1H), 7.30 (d, J = 8.4, 2H), 7.23-7.12 (m, 10H), 6.60 (d, J = 8.4, 2H) , 3.79 (s, 2 H).

Preparation of 5- (4-Fluorophenyl) -2,3-diphenylselenophene

4,5-diphenyl-1,2,3-selenadiazole (57.04 mg, 0.2 mmol), 1-ethynyl-4-fluorobenzene (0.028 mL, 0.24 mmol), [Rh (COD) Cl] ₂ (2.0 mg) in DCE solvent , 0.004 mmol) and DPEPhos (5.4 mg, 0.01 mmol) were added and then reacted at 130 ° C. for 30 minutes. After completion of the reaction, the solvent is removed using an evaporator. The column (Ethyl acetate: Haxane = 1: 50) was obtained to obtain 5- (4-fluorophenyl) -2,3-diphenylselenophene (58.9 mg, 78%) as a desired compound. ¹ H NMR (400 MHz, CDCl ₃ ) d 7.56-7.53 (m, 2H), 7.50 (s, 1H), 7.31-7.23 (m, 10H), 7.10-7.06 (m, 2H).

Preparation of 5- (4-Bromophenyl) -2,3-diphenylselenophene

4,5-diphenyl-1,2,3-selenadiazole (57.04 mg, 0.2 mmol), 1-bromo-4-ethynylbenzene (43.4 mg, 0.24 mmol), [Rh (COD) Cl] ₂ (2.0 mg) in DCE solvent , 0.004 mmol) and DPEPhos (5.4 mg, 0.01 mmol) were added and then reacted at 130 ° C. for 30 minutes. After completion of the reaction, the solvent is removed using an evaporator. The column (Ether: Haxane = 1: 40) was obtained to obtain 5- (4-bromophenyl) -2,3-diphenylselenophene (76.9 mg, 90%) as a desired compound. ¹ H NMR (400 MHz, CDCl ₃ ) d 7.57 (s, 1H), 7.52-7.49 (m, 2H), 7.46-7.43 (m, 2H), 7.31-7.22 (m, 10H).

Preparation of 2,3-Diphenyl-5- (4- (trifluoromethyl) phenyl) selenophene

4,5-diphenyl-1,2,3-selenadiazole (57.04 mg, 0.2 mmol), 1-ethynyl-4- (trifluoromethyl) -benzene (0.039 mL, 0.24 mmol), [Rh (COD) Cl] in DCE solvent ₂ (2.0 mg, 0.004 mmol) and DPEPhos (5.4 mg, 0.01 mmol) were added, followed by reaction at 130 ° C. for 30 minutes. After completion of the reaction, the solvent is removed using an evaporator. The column (Ethyl acetate: Haxane = 1: 50) was obtained to obtain a desired compound, 2,3-diphenyl-5- (4- (trifluoromethyl) phenyl) selenophene (76.9 mg, 90%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.71-7.62 (m, 6H), 7.31-7.24 (m, 9H).

Preparation of 4- (4,5-Diphenylselenophen-2-yl) benzonitrile

4,5-diphenyl-1,2,3-selenadiazole (57.04 mg, 0.2 mmol), 4-ethynylbenzonitrile (30.5 mg, 0.24 mmol), [Rh (COD) Cl] ₂ (2.0 mg, 0.004 mmol) in DCE solvent , DPEPhos (5.4 mg, 0.01 mmol) was added, followed by reaction at 130 ° C. for 30 minutes. After completion of the reaction, the solvent is removed using an evaporator. The column (Ethyl acetate: Haxane = 1: 40) was obtained to obtain 4- (4,5-diphenylselenophen-2-yl) benzonitrile (69.9 mg, 91%) as a desired compound. ¹ H NMR (400 MHz, CDCl ₃ ) d 7.71-7.66 (m, 6H), 7.29-7.26 (m, 9H).

Preparation of 5- (4-Nitrophenyl) -2,3-diphenylselenophene

4,5-diphenyl-1,2,3-selenadiazole (57.04 mg, 0.2 mmol), 1-ethynyl-4-nitrobenzene (35.3 mg, 0.24 mmol), [Rh (COD) Cl] ₂ (2.0 mg) in DCE solvent , 0.004 mmol) and DPEPhos (5.4 mg, 0.01 mmol) were added and then reacted at 130 ° C. for 30 minutes. After completion of the reaction, the solvent is removed using an evaporator. The column (Ethyl acetate: Haxane = 1: 30) was obtained to obtain 5- (4-nitrophenyl) -2,3-diphenylselenophene (69.5 mg, 86%) as a desired compound. ¹ H NMR (400 MHz, CDCl ₃ ) d 8.25 (d, J = 8.8, 2H), 7.75 (s, 1H), 7.71 (d, J = 8.8, 2H), 7.30-7.27 (m, 10H).

Preparation of 2- (4,5-Diphenylselenophen-2-yl) thiophene

4,5-diphenyl-1,2,3-selenadiazole (57.04 mg, 0.2 mmol), 2-ethynylthiophene (0.023 mL, 0.24 mmol), [Rh (COD) Cl] ₂ (2.0 mg, 0.004 mmol) in DCE solvent , DPEPhos (5.4 mg, 0.01 mmol) was added, followed by reaction at 130 ° C. for 30 minutes. After completion of the reaction, the solvent is removed using an evaporator. The column (Ethyl acetate: Haxane = 1: 50) was obtained to obtain 2- (4,5-diphenylselenophen-2-yl) thiophene (54.1 mg, 74%) as a desired compound. ¹ H NMR (400 MHz, CDCl ₃ ) d 7.44 (s, 1H), 7.31-7.22 (m, 11H), 7.17-7.15 (m, 1H), 7.03-7.01 (m, 1H).

Preparation of 2- (4,5-Diphenylselenophen-2-yl) pyridine

4,5-diphenyl-1,2,3-selenadiazole (57.04 mg, 0.2 mmol), 2-ethynylpyridine (0.024 mL, 0.24 mmol), [Rh (COD) Cl] ₂ (2.0 mg, 0.004 mmol) in DCE solvent , DPEPhos (5.4 mg, 0.01 mmol) was added, followed by reaction at 130 ° C. for 30 minutes. After completion of the reaction, the solvent is removed using an evaporator. The column (Ethyl acetate: Haxane = 1: 50) was obtained to obtain 2- (4,5-diphenylselenophen-2-yl) pyridine (24.5 mg, 34%) as a desired compound. ¹ H NMR (400 MHz, CDCl ₃ ) d 8.56-8.54 (m, 1H), 7.85 (s, 1H), 7.71-7.67 (m, 2H), 7.33-7.23 (m, 10H), 7.19-7.12 (m , 1H).

Preparation of 5-Hexyl-2,3-diphenylselenophene

4,5-diphenyl-1,2,3-selenadiazole (57.04 mg, 0.2 mmol), 1-octyne (0.035 mL, 0.24 mmol), [Rh (COD) Cl] ₂ (2.0 mg, 0.004 mmol) in DCE solvent , DPEPhos (5.4 mg, 0.01 mmol) was added, followed by reaction at 130 ° C. for 30 minutes. After completion of the reaction, the solvent is removed using an evaporator. And column (Ethyl acetate: Haxane = 1: 50) was carried out to obtain the desired compound 5-hexyl-2,3-diphenylselenophene (66.9 mg, 91%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.25-7.18 (m, 10H), 7.08-7.06 (m, 1H), 2.89 (t, J = 7.2, 2H), 1.76-1.68 (m, 2H), 1.48 -1.40 (m, 2H), 1.36-1.31 (m, 2H), 0.90 (t, J = 7.1, 3H).

Preparation of 5-Octyl-2,3-diphenylselenophene

4,5-diphenyl-1,2,3-selenadiazole (57.04 mg, 0.2 mmol), 1-decyne (0.043 mL, 0.24 mmol), [Rh (COD) Cl] 2 (2.0 mg, 0.004 mmol) in DCE solvent , DPEPhos (5.4 mg, 0.01 mmol) was added, followed by reaction at 130 ° C. for 30 minutes. After completion of the reaction, remove the solvent using evaporator. And column (Ethyl acetate: Haxane = 1: 50) was carried out to obtain the desired compound 5-octyl-2,3-diphenylselenophene (75.1 mg, 95%). 1 H NMR (400 MHz, CDCl 3) d 7.24-7.16 (m, 10H), 7.07 (s, 1H), 2.88 (t, J = 7.6, 2H), 1.76-1.68 (m, 2H), 1.47-1.29 (m , 10H), 0.89 (t, J = 6.7, 3H).

Preparation of 5- (2-Bromoethyl) -2,3-diphenylselenophene

4,5-diphenyl-1,2,3-selenadiazole (57.04 mg, 0.2 mmol), 4-bromo-1-butyne (0.023 mL, 0.24 mmol), [Rh (COD) Cl] ₂ (2.0 mg) in DCE solvent , 0.004 mmol) and DPEPhos (5.4 mg, 0.01 mmol) were added and then reacted at 130 ° C. for 30 minutes. After completion of the reaction, the solvent is removed using an evaporator. The column (Ethyl acetate: Haxane = 1: 50) was carried out to obtain 5- (2-bromoethyl) -2,3-diphenylselenophene (64.0 mg, 82%) as a desired compound. ¹ H NMR (400 MHz, CDCl ₃ ) d 7.28-7.20 (m, 10H), 7.18 (t, J = 0.9, 1H), 3.78 (t, J = 7.1, 2H), 3.34 (td, J = 10.7, 0.9, 2H).

Preparation of 4- (4,5-Diphenylselenophen-2-yl) butanenitrile

4,5-diphenyl-1,2,3-selenadiazole (57.04 mg, 0.2 mmol), 5-hexynenitrile (0.025 mL, 0.24 mmol), [Rh (COD) Cl] ₂ (2.0 mg, 0.004 mmol) in DCE solvent , DPEPhos (5.4 mg, 0.01 mmol) was added, followed by reaction at 130 ° C. for 30 minutes. After completion of the reaction, the solvent is removed using an evaporator. The column (Ethyl acetate: Haxane = 1: 50) was obtained to obtain 4- (4,5-diphenylselenophen-2-yl) butanenitrile (67.3 mg, 96%) as a desired compound. ¹ H NMR (400 MHz, CDCl ₃ ) d 7.26-7.22 (m, 10H), 7.14 (s, 1H), 3.08 (t, J = 7.2, 2H), 2.48 (t, J = 7.1, 2H), 2.11 -2.04 (m, 2 H).

Preparation of 5-Allyl-2,3-diphenylselenophene

4,5-diphenyl-1,2,3-selenadiazole (57.04 mg, 0.2 mmol), pent-1-en-4-yne (0.023 mL, 0.24 mmol), [Rh (COD) Cl] ₂ ( 2.0 mg, 0.004 mmol) and DPEPhos (5.4 mg, 0.01 mmol) were added, followed by reaction at 130 ° C. for 30 minutes. After completion of the reaction, the solvent is removed using an evaporator. And column (Ethyl acetate: Haxane = 1: 50) was carried out to obtain the desired compound 5-allyl-2,3-diphenylselenophene (58.8 mg, 91%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.25-7.17 (m, 10H), 7.09 (s, 1H), 5.98-5.88 (m, 1H), 5.17-5.04 (m, 2H), 3.00 (t, J = 7.6, 2H), 2.51-2.46 (m, 2H).

Preparation of (4,5-Diphenylselenophen-2-yl) methyl acetate

4,5-diphenyl-1,2,3-selenadiazole (57.04 mg, 0.2 mmol), propargyl acetate (0.024 mL, 0.24 mmol), [Rh (COD) Cl] ₂ (2.0 mg, 0.004 mmol) in DCE solvent, After adding DPEPhos (5.4 mg, 0.01 mmol), the mixture was reacted at 130 ° C. for 30 minutes. After completion of the reaction, the solvent is removed using an evaporator. The column (Ethyl acetate: Haxane = 1: 40) was obtained to obtain the desired compound (4,5-diphenylselenophen-2-yl) methyl acetate (64.7 mg, 91%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.36 (s, 1H), 7.26-7.23 (m, 10H), 5.30-5.28 (m, 2H), 2.13 (s, 3H).

Preparation of 2-Octyl-4,5,6,7-tetrahydrobenzo [ b ] selenophene

4,5,6,7-tetrahydrobenzo [d] [1,2,3] selenadiazole (37.42 mg, 0.2 mmol), 1-decyne (0.043 mL, 0.24 mmol), [Rh (COD) Cl] _{2 in} DCE solvent (2.0 mg, 0.004 mmol) and DPEPhos (5.4 mg, 0.01 mmol) were added, followed by reaction at 130 ° C. for 30 minutes. After completion of the reaction, the solvent is removed using an evaporator. Then, the column (Ethyl acetate: Haxane = 1: 50) was carried out to obtain 2-octyl-4,5,6,7-tetrahydro-benzo [ b ] selenophene (54.7 mg, 92%). ¹ H NMR (400 MHz, CDCl ₃ ) d 6.57 (s, 1H), 2.78-2.74 (m, 4H), 2.53-2.49 (m, 2H), 1.84-1.73 (m, 4H), 1.66-1.58 (m , 2H), 1.38-1.27 (m, 10H), 0.88 (t, J = 6.9, 3H).

Preparation of 2-Octyl-4,5-dihydronaphtho [2,1- b ] selenophene

4,5-dihydronaphtho [1,2- d ] [1,2,3] selenadiazole (47.43 mg, 0.2 mmol), 1-decyne (0.043 mL, 0.24 mmol), [Rh (COD) Cl] _{2 in} DCE solvent (2.0 mg, 0.004 mmol) and DPEPhos (5.4 mg, 0.01 mmol) were added, followed by reaction at 130 ° C. for 30 minutes. After completion of the reaction, the solvent is removed using an evaporator. And column (Ethyl acetate: Haxane = 1: 50) was carried out to obtain the desired compound 2-octyl-4,5-dihydronaphtho [2,1- b ] selenophene (68.4 mg, 99%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.60 (d, J = 7.5, 1H), 7.39 (s, 1H), 7.28-7.24 (m, 2H), 7.18-7.12 (m, 1H), 2.97-2.83 (m, 6H), 1.73-1.66 (m, 2H), 1.42-1.27 (m, 10H), 0.88 (t, J = 6.8, 3H).

Preparation of 3- (4-Chlorophenyl) -5-octyl-2-phenylselenophene

4- (4-chlorophenyl) -5-phenyl-1,2,3-selenadiazole (63.93 mg, 0.2 mmol), 1-decyne (0.043 mL, 0.24 mmol), [Rh (COD) Cl] ₂ ( 2.0 mg, 0.004 mmol) and DPEPhos (5.4 mg, 0.01 mmol) were added, followed by reaction at 130 ° C. for 30 minutes. After completion of the reaction, the solvent is removed using an evaporator. The column (Ethyl acetate: Haxane = 1: 10) was obtained to obtain 3- (4-chlorophenyl) -5-octyl-2-phenylselenophene (82.5 mg, 96%) as a desired compound. ¹ H NMR (400 MHz, CDCl ₃ ) d 7.25-7.12 (m, 9H), 7.05, 7.03 (s, 1H, 0.39: 0.61), 2.88 (t, J = 7.6, 2H), 1.75-1.67 (m, 2H), 1.44-1.39 (m, 2H), 1.33-1.25 (m, 8H), 0.89 (t, J = 6.8, 3H).

Preparation of 2- (4-Chlorophenyl) -5-octyl-3-phenylselenophene

4- (4-chlorophenyl) -5-phenyl-1,2,3-selenadiazole (63.93 mg, 0.2 mmol), 1-decyne (0.043 mL, 0.24 mmol), [Rh (COD) Cl] ₂ ( 2.0 mg, 0.004 mmol) and DPEPhos (5.4 mg, 0.01 mmol) were added, followed by reaction at 130 ° C. for 30 minutes. After completion of the reaction, the solvent is removed using an evaporator. The column (Ethyl acetate: Haxane = 1: 10) was obtained to obtain 2- (4-chlorophenyl) -5-octyl-3-phenylselenophene (79.1 mg, 92%) as a desired compound. ¹ H NMR (400 MHz, CDCl ₃ ) d 7.30-7.12 (m, 9H), 7.06, 7.03 (s, 1H, 0.50: 0.50), 2.88 (t, J = 7.5, 2H), 1.75-1.67 (m, 2H), 1.45-1.28 (m, 10H), 0.89 (t, J = 6.8, 3H).

Preparation of 2,3-Bis (4-chlorophenyl) -5-octylselenophene

4,5-bis (4-chlorophenyl) -1,2,3-selenadiazole (70.82 mg, 0.2 mmol), 1-decyne (0.043 mL, 0.24 mmol), [Rh (COD) Cl] ₂ (2.0) in DCE solvent mg, 0.004 mmol) and DPEPhos (5.4 mg, 0.01 mmol) are added, followed by reaction at 130 ° C. for 30 minutes. After completion of the reaction, the solvent is removed using an evaporator. The column (Ethyl acetate: Haxane = 1: 20) was obtained to obtain a desired compound, 2,3-bis (4-chlorophenyl) -5-octylselenophene (92.9 mg, 99%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.25-7.11 (m, 8H), 7.02 (s, 1H), 2.87 (t, J = 7.6, 2H), 1.72-1.67 (m, 2H), 1.44-1.39 (m, 2H), 1.35-1.28 (m, 8H), 0.89 (t, J = 6.8, 3H).

Preparation of 3- (4-Methoxyphenyl) -5-octyl-2-phenylselenophene

4- (4-methoxyphenyl) -5-phenyl-1,2,3-selenadiazole (63.05 mg, 0.2 mmol), 1-decyne (0.043 mL, 0.24 mmol), [Rh (COD) Cl] ₂ ( 2.0 mg, 0.004 mmol) and DPEPhos (5.4 mg, 0.01 mmol) were added, followed by reaction at 130 ° C. for 30 minutes. After completion of the reaction, the solvent is removed using an evaporator. The column (Ethyl acetate: Haxane = 1: 50) was obtained to obtain 3- (4-methoxyphenyl) -5-octyl-2-phenylselenophene (78.3 mg, 92%) as a desired compound. ¹ H NMR (400 MHz, CDCl ₃ ) d 7.24-7.13 (m, 7H), 7.040, 7.037 (s, 1H), 6.80-6.73 (m, 2H), 3.78, 3.77 (s, 3H, 1.68: 1.32) , 2.87 (t, J = 7.6, 2H), 1.75-1.67 (m, 2H), 1.46-1.28 (m, 10H), 0.88 (t, J = 6.9, 3H).

Preparation of 2- (4-Methoxyphenyl) -5-octyl-3-phenylselenophene

5- (4-methoxyphenyl) -4-phenyl-1,2,3-selenadiazole (63.05 mg, 0.2 mmol), 1-decyne (0.043 mL, 0.24 mmol), [Rh (COD) Cl] ₂ ( 2.0 mg, 0.004 mmol) and DPEPhos (5.4 mg, 0.01 mmol) were added, followed by reaction at 130 ° C. for 30 minutes. After completion of the reaction, the solvent is removed using an evaporator. The column (Ethyl acetate: Haxane = 1: 50) was obtained to obtain 2- (4-methoxyphenyl) -5-octyl-3-phenylselenophene (84.2 mg, 99%) as a desired compound. ¹ H NMR (400 MHz, CDCl ₃ ) d 7.25-7.13 (m, 7H), 7.040, 7.037 (s, 1H), 6.80-6.73 (m, 2H), 3.78, 3.77 (s, 3H, 1.51: 149) , 2.87 (t, J = 7.6, 2H), 1.75-1.67 (m, 2H), 1.46-1.28 (m, 10H), 0.89 (t, J = 6.9, 3H).

Preparation of 2- (5-Octyl-3-phenylselenophen-2-yl) pyridine

4-phenyl-5- (pyridin-2-yl) -1,2,3-selenadiazole (57.24 mg, 0.2 mmol), 1-decyne (0.043 mL, 0.24 mmol), [Rh (COD) Cl] in DCE solvent ₂ (2.0 mg, 0.004 mmol) and DPEPhos (5.4 mg, 0.01 mmol) were added, followed by reaction at 130 ° C. for 30 minutes. After completion of the reaction, the solvent is removed using an evaporator. The column (Ethyl acetate: Haxane = 1: 50) was obtained to obtain 2- (5-octyl-3-phenylselenophen-2-yl) pyridine (4.0 mg, 5%) as a desired compound. ¹ H NMR (400 MHz, CDCl ₃ ) d 8.50 (d, J = 4.1, 1H), 7.36-7.29 (m, 6H), 7.00 (t, J = 5.7, 2H), 6.90 (d, J = 8.1, 1H), 2.87 (t, J = 7.5, 2H), 1.76-1.68 (m, 2H), 1.42-1.39 (m, 2H), 1.28 (br s, 8H), 0.88 (t, J = 6.6, 3H) .

Preparation of 4- (4- (4-Chlorophenyl) -5-phenylselenophen-2-yl) aniline

5- (4-chlorophenyl) -4-phenyl-1,2,3-selenadiazole (63.93 mg, 0.2 mmol), 4-ethynylaniline (28.1 mg, 0.24 mmol), [Rh (COD) Cl] ₂ (in DCE solvent) 2.0 mg, 0.004 mmol) and DPEPhos (5.4 mg, 0.01 mmol) were added, followed by reaction at 130 ° C. for 30 minutes. After completion of the reaction, the solvent is removed using an evaporator. The column (Ethyl acetate: Haxane = 1: 10) was obtained to obtain 4- (4- (4-chlorophenyl) -5-phenylselenophen-2-yl) aniline (80.9mg, 99%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.40-7.37 (m, 3H), 7.25-7.21 (m, 9H), 6.71-6.67 (m, 2H), 3.78 (s, 2H).

Preparation of 4- (5- (4-Chlorophenyl) -4-phenylselenophen-2-yl) aniline

5- (4-chlorophenyl) -4-phenyl-1,2,3-selenadiazole (63.93 mg, 0.2 mmol), 4-ethynylaniline (28.1 mg, 0.24 mmol), [Rh (COD) Cl] ₂ (in DCE solvent) 2.0 mg, 0.004 mmol) and DPEPhos (5.4 mg, 0.01 mmol) were added, followed by reaction at 130 ° C. for 30 minutes. After completion of the reaction, the solvent is removed using an evaporator. The column (Ethyl acetate: Haxane = 1: 10) was obtained to obtain 4- (5- (4-chlorophenyl) -4-phenylselenophen-2-yl) aniline (80.9 mg, 99%) as a desired compound. ¹ H NMR (400 MHz, CDCl ₃ ) d 7.40 (s, 1H), 7.38 (d, J = 8.4, 2H), 7.30-7.27 (m, 5H), 7.20-7.16 (m, 4H), 6.69 (d , J = 8.4, 2H), 3.79 (s, 2H).

Preparation of 3- (4-Chlorophenyl) -5- (3-methoxyphenyl) -2-phenylselenophene

4- (4-chlorophenyl) -5-phenyl-1,2,3-selenadiazole (63.93 mg, 0.2 mmol), 1-ethynyl-3-methoxybenzene (0.03 mL, 0.24 mmol), [Rh (COD)] in DCE solvent Cl] ₂ (2.0 mg, 0.004 mmol) and DPEPhos (5.4 mg, 0.01 mmol) were added, followed by reaction at 130 ° C. for 30 minutes. After completion of the reaction, the solvent is removed using an evaporator. The column (Ethyl acetate: Haxane = 1: 15) was obtained to obtain 3- (4-chlorophenyl) -5- (3-methoxyphenyl) -2-phenylselenophene (76.3 mg, 90%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.56, 7.53 (s, 1H, 0.31: 0.69), 7.36-7.10 (m, 12H), 6.88-6.85 (m, 1H), 3.862, 3.860 (s, 3H) .

Preparation of 2- (4-Chlorophenyl) -5- (3-methoxyphenyl) -3-phenylselenophene

4- (4-chlorophenyl) -5-phenyl-1,2,3-selenadiazole (63.93 mg, 0.2 mmol), 1-ethynyl-3-methoxybenzene (0.03 mL, 0.24 mmol), [Rh (cod)] in DCE solvent Cl] ₂ (2.0 mg, 0.004 mmol) and DPEPhos (5.4 mg, 0.01 mmol) were added, followed by reaction at 130 ° C. for 30 minutes. After completion of the reaction, the solvent is removed using an evaporator. The column (Ethyl acetate: Haxane = 1: 15) was obtained to obtain a desired compound, 2- (4-chlorophenyl) -5- (3-methoxyphenyl) -3-phenyl-selenophene (77.1 mg, 91%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.56, 7.53 (s, 1 H), 7.36-7.10 (m, 12 H), 6.88-6.85 (m, 1 H), 3.862, 3.860 (s, 3 H).

2. Synthesis according to Equations 5 and 6

Examples for the following selenium ring compounds synthesized according to Formulas 5 and 6 will be described.

Preparation of 3- (4-Octylphenyl) -4,5-diphenyl-2,3-dihydroselenophene

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S , S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-diphenyl-1,2,3- in toluene solvent (1 mL) selenadiazole (57.04 mg, 0.2 mmol) and dec-1-ene (0.12 mL, 0.6 mmol) were added, followed by reaction at 100 ^° C. for 2 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Hexane) was carried out to obtain the desired compound 3-octyl-4,5-diphenyl-2,3-dihydro-selenophene (73.3 mg, 92%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.21-7.09 (m, 8H), 7.06-7.04 (m, 2H), 3.69-3.65 (m, 1H), 3.61-3.54 (m, 1H), 3.18 (dd , J = 10.0, 5.2 Hz, 1H), 1.70-1.59 (m, 1H), 1.49-1.38 (m, 2H), 1.29-1.22 (m, 11H), 0.86 (t, J = 6.9 Hz, 3H).

Preparation of 3-Phenethyl-4,5-diphenyl-2,3-dihydroselenophene

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S , S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-diphenyl-1,2,3- in toluene solvent (1 mL) Selenadiazole (57.04 mg, 0.2 mmol) and but-3-en-1-ylbenzene (0.09 mL, 0.6 mmol) were added, followed by reaction at 100 ^° C. for 2 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: Hexane = 1: 40) was obtained to obtain the desired compound 3-phenethyl-4,5-di-phenyl-2,3-dihydroselenophene (74.0 mg, 95%). ¹ H NMR (400 MHz, CDCl ₃ ) δ 7.26-7.22 (m, 2H), 7.19-7.07 (m, 11H), 7.03-6.98 (m, 2H), 3.73-3.69 (m, 1H), 3.67-3.61 (m , 1H), 3.28-3.24 (m, 1H), 2.79-2.72 (m, 1H), 2.65-2.57 (m, 1H), 2.04-1.94 (m, 1H), 1.86-1.78 (m, 1H).

Preparation of 3- (3-Bromopropyl) -4,5-diphenyl-2,3-dihydroselenophene

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S , S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-diphenyl-1,2,3- in toluene solvent (1 mL) selenadiazole (57.04 mg, 0.2 mmol) and 5-bromopent-1-ene (0.071 mL, 0.6 mmol) were added, followed by reaction at 100 ^° C. for 2 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: Hexane = 1: 50) was obtained to obtain 3- (3-bromopropyl) -4,5-diphenyl-2,3-dihydroselenophene (58 mg, 70%) as a desired compound. ¹ H NMR (400 MHz, CDCl ₃ ) δ 7.22-7.09 (m, 8H), 7.08-7.04 (m, 2H), 3.72-3.61 (m, 2H), 3.38-3.29 (m, 2H), 3.17-3.14 (m , 1H), 2.03-1.87 (m, 2H), 1.86-1.75 (m, 1H), 1.68-1.60 (m, 1H).

Preparation of 3- (Phenoxymethyl) -4,5-diphenyl-2,3-dihydroselenophene

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S , S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-diphenyl-1,2,3- in toluene solvent (1 mL) Selenadiazole (57.04 mg, 0.2 mmol) and (allyloxy) benzene (0.082 mL, 0.6 mmol) are added and the reaction is carried out at 100 ^° C. for 2 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: Hexane = 1: 40) was obtained to obtain the desired compound 3- (phenoxymethyl) -4,5-diphenyl-2,3-dihydroselenophene (64 mg, 85%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.27-7.23 (m, 2H), 7.19-7.11 (m, 10H), 6.94-6.90 (m, 1H), 6.87-6.84 (m, 2H), 4.23 (t, J = 9.4 Hz, 1H), 4.10-4.04 (m, 1H), 3.91-3.88 (m, 1H), 3.83-3.78 (m, 1H), 3.55 (dd, J = 10.5, 3.5 Hz, 1H).

Preparation of 2- (4,5-Diphenyl-2,3-dihydroselenophen-3-yl) ethanol

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S , S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-diphenyl-1,2,3- in toluene solvent (1 mL) Selenadiazole (57.04 mg, 0.2 mmol) and but-3-en-1-ol (0.062 mL, 0.6 mmol) were added, followed by reaction at 100 ^° C. for 2 hours. After the reaction is completed, the solvent is removed using an evaporator. Then proceed to the column (Ether: DCM: Hexane = 1: 2: 3 :) to the desired compound 2- (4,5-diphenyl-2,3-dihydroselenophen-3-yl) ethan-1-ol (58.4 mg, 89 %) Could be obtained. ¹ H NMR (400 MHz, CDCl ₃ ) d 7.21-7.07 (m, 10H), 3.84-3.70 (m, 4H), 3.23-3.20 (m, 1H), 1.98-1.89 (m, 1H), 1.84-1.76 (m , 1H), 1.33-1.31 (m, 1H).

Preparation of 3- (4,5-Diphenyl-2,3-dihydroselenophen-3-yl) propan-1-ol

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S , S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-diphenyl-1,2,3- in toluene solvent (1 mL) Selenadiazole (57.04 mg, 0.2 mmol) and pent-4-en-1-ol (0.052 mL, 0.6 mmol) were added, followed by reaction at 100 ^° C. for 2 hours. After the reaction is completed, the solvent is removed using an evaporator. Then proceed to the column (Ether: DCM: Hexane = 1: 2: 3 :) to the desired compound 3- (4,5-diphenyl-2,3-dihydroselenophen-3-yl) propan-1-ol (61.6 mg, 90 %) Could be obtained. ¹ H NMR (400 MHz, CDCl ₃ ) d 7.21-7.08 (m, 8H), 7.07-7.04 (m, 2H), 3.72-3.68 (m, 1H), 3.67-3.63 (m, 1H), 3.62-3.57 (m , 2H), 3.20-3.17 (m, 1H), 1.77-1.52 (m, 4H).

Preparation of 4- (4,5-Diphenyl-2,3-dihydroselenophen-3-yl) butan-1-ol

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S , S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-diphenyl-1,2,3- in toluene solvent (1 mL) selenadiazole (57.04 mg, 0.2 mmol), hex-5-en-1-ol) 0.072 mL, 0.6 mmol) was added, followed by reaction at 100 ^° C. for 2 hours. After the reaction is completed, the solvent is removed using an evaporator. Then proceed to the column (Ether: DCM: Hexane = 1: 2: 3 :) to the desired compound 4- (4,5-Diphenyl-2,3-dihydroselenophen-3-yl) butan-1-ol (65.1 mg, 91 %) Could be obtained. ¹ H NMR (400 MHz, CDCl ₃ ) d 7.21-7.04 (m, 10H), 3.71-3.66 (m, 1H), 3.63-3.58 (m, 3H), 3.19 (dd, J = 9.9, 5.0 Hz, 1H), 1.74-1.66 (m, 1H), 1.53-1.33 (m, 5H), 1.15-1.14 (m, 1H).

Preparation of (4,5-Diphenyl-2,3-dihydroselenophen-3-yl) methyl) (methyl) sulfane

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S , S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-diphenyl-1,2,3- in toluene solvent (1 mL) selenadiazole (57.04 mg, 0.2 mmol) and allyl (methyl) sulfane (0.066 mL, 0.6 mmol) were added, followed by reaction at 100 ^° C. for 2 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: Hexane = 1: 40) was then obtained to obtain the desired compound ((4,5-Diphenyl-2,3-dihydroselenophen-3-yl) methyl) (methyl) sulfane (50.4 mg, 73%). Could. ¹ H NMR (400 MHz, CDCl ₃ ) d 7.22-7.06 (m, 10H), 3.80-3.71 (m, 2H), 3.52-3.46 (m, 1H), 2.94-2.85 (m, 1H), 2.61-2.57 (m , 1H), 2.07 (s, 3H).

Preparation of ((4,5-Diphenyl-2,3-dihydroselenophen-3-yl) methyl) trimethylsilane

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S , S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-diphenyl-1,2,3- in toluene solvent (1 mL) selenadiazole (57.04 mg, 0.2 mmol) and allyltrimethylsilane (0.095 mL, 0.6 mmol) were added, followed by reaction at 100 ^° C. for 2 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: Hexane = 1: 100) was obtained to obtain a desired compound ((4,5-diphenyl-2,3-dihydroselenophen-3-yl) methyl) trimethylsilane (68.2 mg, 92%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.22-7.02 (m, 10H), 3.74-3.66 (m, 2H), 3.10-3.03 (m, 1H), 1.16-1.08 (m, 1H), 0.78-0.73 (m , 1H), 0.04 (s, 9H).

Preparation of 3,4,5-Triphenyl-2,3-dihydroselenophene

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S , S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-diphenyl-1,2,3- in toluene solvent (1 mL) After adding selenadiazole (57.04 mg, 0.2 mmol) and styrene (0.069 mL, 0.6 mmol), the mixture was reacted at 100 ^° C. for 2 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: Hexane = 1: 50) was obtained to obtain the desired compound 3,4,5-triphenyl-2,3-dihydro-selenophene (65.4 mg, 90%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.45-7.43 (m, 2H), 7.34-7.29 (m, 4H), 7.26-7.19 (m, 4H), 7.03-6.99 (m, 3H), 6.91-6.88 (m , 2H), 4.75 (dd, J = 8.4, 4.3 Hz, 1H), 4.04-4.00 (m, 1H), 3.20 (dd, J = 10.2, 4.4 Hz, 1H).

Preparation of 4,5-Diphenyl-3- ( p -tolyl) -2,3-dihydroselenophene

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S , S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-diphenyl-1,2,3- in toluene solvent (1 mL) selenadiazole (57.04 mg, 0.2 mmol) and 1-methyl-4-vinylbenzene (0.079 mL, 0.6 mmol) were added, followed by reaction at 100 ^° C. for 2 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: Hexane = 1: 20) was obtained to obtain the desired compound, 4,5-diphenyl-3- ( p -tolyl) -2,3-dihydroselenophene (66.8 mg, 89%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.33-7.29 (m, 4H), 7.23-7.19 (m, 3H), 7.12 (d, J = 7.8 Hz, 2H), 7.03-6.99 (m, 3H), 6.92- 6.89 (m, 2H), 4.73-4.70 (m, 1H), 4.03-3.98 (m, 1H), 3.16 (dd, J = 10.2, 4.3 Hz, 1H), 2.32 (s, 3H).

Preparation of 3- (4- ( tert- Butyl) phenyl) -4,5-diphenyl-2,3-dihydroselenophene

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S , S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-diphenyl-1,2,3- in toluene solvent (1 mL) selenadiazole (57.04 mg, 0.2 mmol) and 1- (tert-butyl) -4-vinylbenzene (0.11 mL, 0.6 mmol) were added, followed by reaction at 100 ^° C. for 2 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: Hexane = 1: 50) was obtained to obtain 3- (4- (tert-butyl) phenyl) -4,5-diphenyl-2,3-dihydroselenophene (73.5 mg, 88%) as a desired compound. Could. ¹ H NMR (400 MHz, CDCl ₃ ) d 7.38-7.31 (m, 6H), 7.24-7.20 (m, 3H), 7.04-7.00 (m, 3H), 6.93-6.90 (m, 2H), 4.72-4.69 (m , 1H), 4.06-4.01 (m, 1H), 3.16 (dd, J = 10.1, 3.6 Hz, 1H), 1.31 (s, 9H).

Preparation of 3- (4-Methoxyphenyl) -4,5-diphenyl-2,3-dihydroselenophene

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S , S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-diphenyl-1,2,3- in toluene solvent (1 mL) selenadiazole (57.04 mg, 0.2 mmol) and 1-methoxy-4-vinylbenzene (0.08 mL, 0.6 mmol) were added, followed by reaction at 100 ^° C. for 2 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: Hexane = 1: 20) was obtained to obtain the desired compound 3- (4-methoxyphenyl) -4,5-diphenyl-2,3-dihydroselenophene (77.5 mg, 99%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.37-7.33 (m, 2H), 7.32-7.30 (m, 2H), 7.22-7.20 (m, 3H), 7.03-7.00 (m, 3H), 6.92-6.88 (m , 2H), 6.87-6.83 (m, 2H), 4.70 (dd, J = 8.3, 4.2 Hz, 1H), 4.02-3.98 (m, 1H), 3.78 (s, 3H), 3.15 (dd, J = 10.2 , 4.2 Hz, 1H).

Preparation of 3- (3-Fluorophenyl) -4,5-diphenyl-2,3-dihydroselenophene

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S , S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-diphenyl-1,2,3- in toluene solvent (1 mL) Selenadiazole (57.04 mg, 0.2 mmol) and 1-fluoro-3-vinylbenzene (0.071 mL, 0.6 mmol) are added, followed by reaction at 100 ^° C. for 2 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: Hexane = 1: 50) was obtained to obtain the desired compound 3- (3-fluorophenyl) -4,5-diphenyl-2,3-dihydroselenophene (69.1 mg, 90%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.32-7.24 (m, 3H), 7.23-7.15 (m, 5H), 7.04-6.99 (m, 3H), 6.96-6.88 (m, 3H), 4.74 (dd, J = 8.5, 4.1 Hz, 1H), 4.04-3.99 (m, 1H), 3.17 (dd, J = 10.3, 4.2 Hz, 1H).

Preparation of 3- (4-Chlorophenyl) -4,5-diphenyl-2,3-dihydroselenophene

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S , S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-diphenyl-1,2,3- in toluene solvent (1 mL) selenadiazole (57.04 mg, 0.2 mmol) and 1-chloro-4-vinylbenzene (0.072 mL, 0.6 mmol) are added, followed by reaction at 100 ^° C. for 2 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: Hexane = 1: 50) was obtained to obtain 3- (4-chlorophenyl) -4,5-diphenyl-2,3-dihydroselenophene (65.7 mg, 83%) as a desired compound. ¹ H NMR (400 MHz, CDCl ₃ ) d 7.38-7.36 (m, 2H), 7.31-7.25 (m, 4H), 7.23-7.20 (m, 3H), 7.04-7.00 (m, 3H), 6.89-6.86 (m , 2H), 4.74-4.71 (m, 1H), 4.03-3.98 (m, 1H), 3.14 (dd, J = 10.3, 4.3 Hz, 1H).

Preparation of 3- (3-Bromophenyl) -4,5-diphenyl-2,3-dihydroselenophene

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S , S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-diphenyl-1,2,3- in toluene solvent (1 mL) Selenadiazole (57.04 mg, 0.2 mmol) and 1-bromo-3-vinylbenzene (0.078 mL, 0.6 mmol) were added, followed by reaction at 100 ^° C. for 2 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: Hexane = 1: 50) was obtained to obtain the desired compound, 3- (3-bromophenyl) -4,5-diphenyl-2,3-dihydroselenophene (85.4 mg, 97%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.57 (t, J = 1.8 Hz, 1H), 7.39-7.36 (m, 2H), 7.32-7.29 (m, 2H), 7.24-7.21 (m, 3H), 7.18 ( t, J = 7.8 Hz, 1H), 7.05-7.00 (m, 3H), 6.91-6.87 (m, 2H), 4.70 (dd, J = 8.5, 4.2 Hz, 1H), 4.04-3.99 (m, 1H) , 3.16 (dd, J = 10.3, 4.2 Hz, 1H).

Preparation of 3- (4-Bromophenyl) -4,5-diphenyl-2,3-dihydroselenophene

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S , S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-diphenyl-1,2,3- in toluene solvent (1 mL) selenadiazole (57.04 mg, 0.2 mmol) and 1-bromo-4-vinylbenzene (0.078 mL, 0.6 mmol) were added, followed by reaction at 100 ^° C. for 2 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: Hexane = 1: 50) was obtained to obtain the desired compound 3- (4-bromophenyl) -4,5-diphenyl-2,3-dihydroselenophene (79.3 mg, 90%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.44-7.41 (m, 2H), 7.34-7.27 (m, 4H), 7.23-7.19 (m, 3H), 7.04-6.99 (m, 3H), 6.90-6.85 (m , 2H), 4.70 (dd, J = 8.4, 4.2 Hz, 1H), 4.03-3.97 (m, 1H), 3.17-3.09 (m, 1H).

Preparation of 4- (4,5-Diphenyl-2,3-dihydroselenophen-3-yl) phenyl acetate

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S , S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-diphenyl-1,2,3- in toluene solvent (1 mL) selenadiazole (57.04 mg, 0.2 mmol) and 4-vinylphenyl acetate (0.092 mL, 0.6 mmol) were added, followed by reaction at 100 ^° C. for 2 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: Hexane = 1: 5) was obtained to obtain 4- (4,5-diphenyl-2,3-dihydroselenophen-3-yl) phenyl acetate (37.9 mg, 47%) as a desired compound. ¹ H NMR (400 MHz, CDCl ₃ ) δ 7.45-7.43 (m, 2H), 7.32-7.29 (m, 2H), 7.22-7.20 (m, 3H), 7.05-7.01 (m, 5H), 6.90-6.88 (m , 2H), 4.76-4.73 (m, 1H), 4.04-3.99 (m, 1H), 3.17 (dd, J = 4.1, 10.3 Hz, 1H), 2.28 (s, 3H).

Preparation of 4,5-Bis (4-chlorophenyl) -3- (4-methoxyphenyl) -2,3-dihydroselenophene

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S , S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-bis (4-chlorophenyl) -1 in toluene solvent (1 mL) 2,3-selenadiazole (70.82 mg, 0.2 mmol) and 1-methoxy-4-vinylbenzene (0.08 mL, 0.6 mmol) were added, followed by reaction at 100 ^° C. for 2 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: Hexane = 1: 100) was then obtained to obtain the desired compound 4,5-bis (4-chlorophenyl) -3- (4-methoxyphenyl) -2,3-dihydroselenophene (78.2 mg, 85%). Could. ¹ H NMR (400 MHz, CDCl ₃ ) d 7.29-7.27 (m, 2H), 7.23-7.18 (m, 4H), 7.01-6.98 (m, 2H), 6.86-6.82 (m, 2H), 6.80-6.77 (m , 2H), 4.67-4.63 (m, 1H), 3.98-3.94 (m, 1H), 3.78 (s, 3H), 3.21-3.17 (m, 1H).

Preparation of 3- (4-Methoxy-phenyl) -4,5-dimethyl-2,3-dihydroselenophene

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S , S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-dimethyl-1,2,3- in toluene solvent (1 mL) Selenadiazole (32.22 mg, 0.2 mmol) and 1-methoxy-4-vinylbenzene (0.08 mL, 0.6 mmol) are added and the reaction is carried out at 100 ^° C. for 2 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: Hexane = 1: 50) was obtained to obtain the desired compound 3- (4-methoxy-phenyl) -4,5-dimethyl-2,3-dihydroselenophene (52.9 mg, 99%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.19-7.17 (m, 2H), 6.87-6.85 (m, 2H), 3.99 (t, J = 7.4 Hz, 1H), 3.80 (s, 3H), 3.65-3.60 ( m, 1H), 3.07-3.03 (m, 1H), 2.03 (q, J = 0.9 Hz, 3H), 1.44 (t, J = 0.9 Hz, 3H).

Preparation of 3- (4-Methoxyphenyl) -2,3,4,5,6,7-hexahydrobenzo [b] selenophene

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S , S ) -DIOP (12.0 mg, 0.024 mmol), 4,5,6,7-tetrahydrobenzo [d] in toluene solvent (1 mL) [1,2,3] selenadiazole (37.42 mg, 0.2 mmol) and 1-methoxy-4-vinylbenzene (0.08 mL, 0.6 mmol) were added, followed by reaction at 100 ^° C. for 2 hours. After the reaction is completed, the solvent is removed using an evaporator. Then proceed to the column (Ether: Hexane = 1: 50) to obtain the desired compound 3- (4-methoxyphenyl) -2,3,4,5,6,7-hexahydrobenzo [b] selenophene (58.1 mg, 99%). Could get ¹ H NMR (400 MHz, CDCl ₃ ) d 7.19-7.15 (m, 2H), 6.87-6.84 (m, 2H), 3.97-3.93 (m, 1H), 3.79 (s, 3H), 3.66-3.61 (m, 1H ), 3.09-3.05 (m, 1H), 2.41-2.26 (m, 2H), 1.83-1.67 (m, 4H), 1.62-1.56 (m, 2H).

Preparation of 3- (4-Methoxyphenyl) -2,3,4,5,6,7-hexahydrobenzo [b] selenophene

Toluene solvent (1 mL) [Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S , S ) -DIOP (12.0 mg, 0.024 mmol), 4 H -chromeno [4,3- d ] [ 1,2,3] selenadiazole (47.43 mg, 0.2 mmol) and 1-methoxy-4-vinylbenzene (0.08 mL, 0.6 mmol) are added, followed by reaction at 100 ^° C. for 2 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: Hexane = 1: 50) was processed to obtain 3- (4-methoxyphenyl) -2,3,4,5,6,7-hexahydrobenzo [b] selenophene (59.7 mg, 87%) as a desired compound. Could get ¹ H NMR (400 MHz, CDCl ₃ ) d 7.27-7.25 (m, 2H), 7.01-6.97 (m, 1H), 6.86-6.83 (m, 2H), 6.82-6.79 (m, 1H), 6.70-6.64 (m , 2H), 5.09 (d, J = 1.7 Hz, 2H), 4.61-4.58 (m, 1H), 4.06-4.01 (m, 1H), 3.77 (s, 3H), 3.22 (dd, J = 10.2, 3.1 Hz, 1H).

Preparation of 4-Phenethyl-2,3-diphenylselenophene

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S , S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-diphenyl-1,2,3- in toluene solvent (1 mL) Selenadiazole (57.04 mg, 0.2 mmol) and but-3-en-1-ylbenzene (0.09 mL, 0.6 mmol) were added, followed by reaction at 100 ^° C. for 2 hours. Confirm that the reaction is complete by TLC and add DDQ (68.1 mg, 0.3 mmol) dissolved in toluene (1.5 mL). The reaction solution is stirred at 100 ^° C. for 10 minutes. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: Hexane = 1: 50) can be obtained to obtain the desired compound, 4-phenethyl-2,3-diphenylselenophene (63.5 mg, 82%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.62 (t, J = 23.0 Hz, 1H), 7.34-7.28 (m, 3H), 7.26-7.12 (m, 10H), 6.99-6.97 (m, 2H), 2.70 ( s, 4H).

Preparation of 4- (Phenoxymethyl) -2,3-diphenylselenophene

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S , S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-diphenyl-1,2,3- in toluene solvent (1 mL) Selenadiazole (57.04 mg, 0.2 mmol) and (allyloxy) benzene (0.082 mL, 0.6 mmol) are added and the reaction is carried out at 100 ^° C. for 2 hours. Confirm that the reaction is complete by TLC and add DDQ (68.1 mg, 0.3 mmol) dissolved in toluene (1.5 mL). The reaction solution is stirred at 100 ^° C. for 10 minutes. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: Hexane = 1: 50) can be obtained to obtain 4- (phenoxymethyl) -2,3-diphenylselenophene (46.7 mg, 60%) as a desired compound. ¹ H NMR (400 MHz, CDCl ₃ ) d 8.08 (t, J = 22.5 Hz, 1H), 7.30-7.22 (m, 8H), 6.93 (t, J = 7.3 Hz, 1H), 6.90 (d, J = 8.6 Hz , 2H), 4.74 (s, 2H).

Preparation of 2,3,4-Triphenylselenophene

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S , S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-diphenyl-1,2,3- in toluene solvent (1 mL) After adding selenadiazole (57.04 mg, 0.2 mmol) and styrene (0.069 mL, 0.6 mmol), the mixture was reacted at 100 ^° C. for 2 hours. Confirm that the reaction is complete by TLC and add DDQ (68.1 mg, 0.3 mmol) dissolved in toluene (1.5 mL). The reaction solution is stirred at 100 ^° C. for 10 minutes. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: Hexane = 1: 50) was obtained to obtain the desired compound 2,3,4-triphenylselenophene (57.5 mg, 80%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.42 (t, J = 22.5 Hz, 1H), 7.20-7.16 (m, 8H), 7.15-7.10 (m, 3H), 7.08-7.06 (m, 2H), 6.97- 6.94 (m, 2 H).

Preparation of 2,3-Diphenyl-4- ( p -tolyl) selenophene

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S , S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-diphenyl-1,2,3- in toluene solvent (1 mL) selenadiazole (57.04 mg, 0.2 mmol) and 1-methyl-4-vinylbenzene (0.079 mL, 0.6 mmol) were added, followed by reaction at 100 ^° C. for 2 hours. Confirm that the reaction is complete by TLC and add DDQ (68.1 mg, 0.3 mmol) dissolved in toluene (1.5 mL). The reaction solution is stirred at 100 ^° C. for 10 minutes. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: Hexane = 1: 40) was obtained to obtain the desired compound, 2,3-diphenyl-4- ( p -tolyl) selenophene (68.7 mg, 92%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.88 (t, J = 22.9 Hz, 1H), 7.25-7.11 (m, 8H), 7.00-6.95 (m, 6H), 2.28 (s, 3H).

Preparation of 4- (4-Methoxyphenyl) -2,3-diphenylselenophene

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S , S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-diphenyl-1,2,3- in toluene solvent (1 mL) selenadiazole (57.04 mg, 0.2 mmol) and 1-methoxy-4-vinylbenzene (0.08 mL, 0.6 mmol) were added, followed by reaction at 100 ^° C. for 2 hours. Confirm that the reaction is complete by TLC and add DDQ (68.1 mg, 0.3 mmol) dissolved in toluene (1.5 mL). The reaction solution is stirred at 100 ^° C. for 10 minutes. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: Hexane = 1: 50) can be obtained to obtain 4- (4-methoxyphenyl) -2,3-diphenylselenophene (63.9 mg, 82%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.84 (t, J = 22.8 Hz, 1H), 7.17-7.11 (m, 8H), 6.99-6.95 (m, 4H), 6.71 (d, J = 8.6 Hz, 2H) , 3.75 (s, 3 H).

Preparation of 4- (3-Bromophenyl) -2,3-diphenylselenophene

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S , S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-diphenyl-1,2,3- in toluene solvent (1 mL) Selenadiazole (57.04 mg, 0.2 mmol) and 1-bromo-3-vinylbenzene (0.078 mL, 0.6 mmol) were added, followed by reaction at 100 ^° C. for 2 hours. Confirm that the reaction is complete by TLC and add DDQ (68.1 mg, 0.3 mmol) dissolved in toluene (1.5 mL). The reaction solution is stirred at 100 ^° C. for 10 minutes. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: Hexane = 1: 50) was obtained to obtain 4- (3-bromophenyl) -2,3-diphenylselenophene (67.5 mg, 77%) as a desired compound. ¹ H NMR (400 MHz, CDCl ₃ ) d 7.93 (t, J = 22.2 Hz, 1H), 7.31-7.30 (m, 2H), 7.20-7.13 (m, 8H), 7.01-6.94 (m, 3H), 6.90- 6.87 (m, 1 H).

Preparation of 4- (4-Methoxyphenyl) -2,3-dimethylselenophene

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S , S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-dimethyl-1,2,3- in toluene solvent (1 mL) Selenadiazole (32.22 mg, 0.2 mmol) and 1-methoxy-4-vinylbenzene (0.08 mL, 0.6 mmol) are added and the reaction is carried out at 100 ^° C. for 2 hours. Confirm that the reaction is complete by TLC and add DDQ (68.1 mg, 0.3 mmol) dissolved in toluene (1.5 mL). The reaction solution is stirred at 100 ^° C. for 10 minutes. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: Hexane = 1: 50) can be obtained to obtain the desired compound, 4- (4-methoxyphenyl) -2,3-dimethylselenophene (44.0 mg, 83%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.49 (t, J = 22.7 Hz, 1H), 7.25-7.24 (m, 2H), 6.93-6.90 (m, 2H), 3.84 (s, 3H), 2.49 (s, 3H), 2.02 (s, 3H).

3. Synthesis by Equation 6, 7, 8

The synthesis method for the following compounds synthesized according to Formulas 6, 7, and 8 will be described in more detail.

(E) Preparation of -4,5-diphenyl-3-styryl-2,3-dihydroselenophene

In dioxane solvent (1 mL) [Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( rac ) -BINAP (14.9 mg, 0.024 mmol), 4,5-diphenyl-1,2,3-selenadiazole ( 57.04 mg, 0.2 mmol) and (E) -buta-1,3-dien-1-ylbenzene (78 mg, 0.6 mmol) were added and then reacted at 130 ^° C. for 3 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Acetone: Hexane = 1: 30) was obtained to obtain the desired compound (E) -4,5-diphenyl-3-styryl-2,3-dihydroselenophene (63.5 mg, 82%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.37-7.27 (m, 4H), 7.24-7.16 (m, 6H), 7.12-7.10 (m, 5H), 6.58 (d, J = 15.9 Hz, 1H), 6.49 (dd, J = 15.8, 7.9 Hz, 1H), 4.28 (td, J = 11.6, 4.7 Hz, 1H), 3.79 (dd, J = 10.2, 7.7 Hz, 1H), 3.20 (dd, J = 10.2, 4.7 Hz, 1H).

(E) - 3- (3,4- dichlorostyryl) Preparation of -4,5-diphenyl-2,3-dihydroselenophene

In dioxane solvent (1 mL) [Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( rac ) -BINAP (14.9 mg, 0.024 mmol), 4,5-diphenyl-1,2,3-selenadiazole ( 57.04 mg, 0.2 mmol), (E) -4- (buta-1,3-dien-1-yl) -1,2-dichlorobenzene (78 mg, 0.6 mmol) were added and then 130 ^° C. for 3 hours. React. After the reaction is completed, the solvent is removed using an evaporator. The column (Acetone: Hexane = 1: 30) was then run to obtain the desired compound (E) -3- (3,4-dichlorostyryl) -4,5-diphenyl-2,3-dihydroselenophene (71.8 mg, 79%). Could get ¹ H NMR (400 MHz, CDCl ₃ ) d 7.41 (d, J = 2.0 Hz, 1H), 7.32 (d, J = 8.4 Hz, 1H), 7.23-7.08 (m, 11H), 6.48-6.35 (m, 2H), 4.27 (td, J = 7.1, 4.5 Hz, 1H), 3.78 (dd, J = 10.2, 7.7 Hz, 1H), 3.17 (dd, J = 10.2, 4.4 Hz, 1H).

Preparation of (E) -2,3-diphenyl-4-styrylselenophene

In dioxane solvent (1 mL) [Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( rac ) -BINAP (14.9 mg, 0.024 mmol), 4,5-diphenyl-1,2,3-selenadiazole ( 57.04 mg, 0.2 mmol) and (E) -buta-1,3-dien-1-ylbenzene (78 mg, 0.6 mmol) were added and then reacted at 130 ^° C. for 3 hours. After cooling to room temperature, DDQ (90.8 mg, 0.4 mmol) and Toluene (1.0 mL) are added and allowed to react at room temperature for 10 minutes. After the reaction is completed, the solvent is removed using an evaporator. The column (Acetone: Hexane = 1: 30) was obtained to obtain the desired compound (E) -2,3-diphenyl-4-styrylselenophene (73.3 mg, 92%). ¹ H NMR (400 MHz, CDCl ₃ ) d 8.11 (s, 1H), 7.29-7.15 (m, 15H), 6.90 (d, J = 16.2 Hz, 1H), 6.70 (d, J = 16.2 Hz, 1H) .

(E) Preparation of -4- (3-methylstyryl) -2,3-diphenylselenophene

In dioxane solvent (1 mL) [Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( rac ) -BINAP (14.9 mg, 0.024 mmol), 4,5-diphenyl-1,2,3-selenadiazole ( 57.04 mg, 0.2 mmol) and (E) -1- (buta-1,3-dien-1-yl) -4-methylbenzene (86.5 mg, 0.6 mmol) were added and reacted at 130 ^° C. for 3 hours. . After cooling to room temperature, DDQ (90.8 mg, 0.4 mmol) and Toluene (1.0 mL) are added and allowed to react at room temperature for 10 minutes. After the reaction is completed, the solvent is removed using an evaporator. The column (Acetone: Hexane = 1: 30) was obtained to obtain the desired compound (E) -2,3-diphenyl-4-styrylselenophene (73.3 mg, 92%). ¹ H NMR (400 MHz, CDCl ₃ ) d 8.12 (s, 1H), 7.34-7.29 (m, 3H), 7.21-7.13 (m, 10H), 7.02 (d, J = 7.0 Hz, 1H), 6.88 ( d, J = 16.2 Hz, 1H), 6.69 (d, J = 16.2 Hz, 1H).

(E) Preparation of -4- (4-methylstyryl) -2,3-diphenylselenophene

In dioxane solvent (1 mL) [Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( rac ) -BINAP (14.9 mg, 0.024 mmol), 4,5-diphenyl-1,2,3-selenadiazole ( 57.04 mg, 0.2 mmol) and (E) -1- (buta-1,3-dien-1-yl) -4-methylbenzene (78 mg, 0.6 mmol) were added and reacted at 130 ^° C. for 3 hours. . After cooling to room temperature, DDQ (90.8 mg, 0.4 mmol) and Toluene (1.0 mL) are added and allowed to react at room temperature for 10 minutes. After the reaction is completed, the solvent is removed using an evaporator. The column (Acetone: Hexane = 1: 30) was obtained to obtain the desired compound (E) -2,3-diphenyl-4-styrylselenophene (47.5 mg, 70%). ¹ H NMR (400 MHz, CDCl ₃ ) d 8.11 (s, 1H), 7.31-7.30 (m, 3H), 7.25-7.14 (m, 9H), 7.08 (d, J = 8.0 Hz, 2H), 6.89 ( d, J = 16.2 Hz, 1H), 6.65 (d, J = 16.2 Hz, 1H).

(E) Preparation of -4- (4-methoxystyryl) -2,3-diphenylselenophene

In dioxane solvent (1 mL) [Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( rac ) -BINAP (14.9 mg, 0.024 mmol), 4,5-diphenyl-1,2,3-selenadiazole ( 1a , 57.04 mg, 0.2 mmol), (E) -1- (buta-1,3-dien-1-yl) -4-methoxybenzene ( 2a , 96.2 mg, 0.6 mmol) was added, followed by 130 ^o C. Let it react for 3 hours. After cooling to room temperature, DDQ (90.8 mg, 0.4 mmol) and Toluene (1.0 mL) are added and allowed to react at room temperature for 10 minutes. After the reaction is completed, the solvent is removed using an evaporator. And columns (Acetone: Hexane = 1: 30 ) was able to proceed to obtain the desired compound (E) -4- (4-methoxystyryl ) -2,3-diphenylselenophene (3aa, 65.6 mg, 79%). ¹ H NMR (400 MHz, CDCl ₃ ) d 8.08 (s, 1H), 7.31-7.16 (m, 13H), 6.86 (d, J = 16.2 Hz, 1H), 6.81 (d, J = 8.7 Hz, 2H) , 6.57 (d, J = 16.2 Hz, 1H), 3.79 (s, 3H).

(E) Preparation of -4- (2-chlorostyryl) -2,3-diphenylselenophene

In dioxane solvent (1 mL) [Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( rac ) -BINAP (14.9 mg, 0.024 mmol), 4,5-diphenyl-1,2,3-selenadiazole ( 57.04 mg, 0.2 mmol) and (E) -1- (buta-1,3-dien-1-yl) -2-chlorobenzene (98.8 mg, 0.6 mmol) were added and then reacted at 130 ^° C. for 3 hours. . After cooling to room temperature, DDQ (90.8 mg, 0.4 mmol) and Toluene (1.0 mL) are added and allowed to react at room temperature for 10 minutes. After the reaction is completed, the solvent is removed using an evaporator. The column (Acetone: Hexane = 1: 30) was obtained to obtain the desired compound (E) -4- (2-chlorostyryl) -2,3-diphenylselenophene (67.1 mg, 80%). ¹ H NMR (400 MHz, CDCl ₃ ) d 8.22 (s, 1H), 7.38-7.11 (m, 15H), 6.68 (d, J = 16.2 Hz, 1H).

(E) Preparation of -4- (4-chlorostyryl) -2,3-diphenylselenophene

In dioxane solvent (1 mL) [Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( rac ) -BINAP (14.9 mg, 0.024 mmol), 4,5-diphenyl-1,2,3-selenadiazole ( 57.04 mg, 0.2 mmol) and (E) -1- (buta-1,3-dien-1-yl) -4-chlorobenzene (98.8 mg, 0.6 mmol) were added and reacted at 130 ^° C. for 3 hours. . After cooling to room temperature, DDQ (90.8 mg, 0.4 mmol) and Toluene (1.0 mL) are added and reacted at room temperature for 10 minutes. After the reaction is completed, the solvent is removed using an evaporator. The column (Acetone: Hexane = 1: 30) was obtained to obtain the desired compound (E) -4- (4-chlorostyryl) -2,3-diphenylselenophene (52.1 mg, 62%). ¹ H NMR (400 MHz, CDCl ₃ ) d 8.14 (s, 1H), 7.32-7.14 (m, 14H), 6.84 (d, J = 16.2 Hz, 1H), 6.67 (d, J = 16.2 Hz, 1H) .

(E) Preparation of -4- (3-bromostyryl) -2,3-diphenylselenophene

In dioxane solvent (1 mL) [Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( rac ) -BINAP (14.9 mg, 0.024 mmol), 4,5-diphenyl-1,2,3-selenadiazole ( 57.04 mg, 0.2 mmol) and (E) -1-bromo-3- (buta-1,3-dien-1-yl) benzene (125.5 mg, 0.6 mmol) were added and then reacted at 130 ^° C. for 3 hours. Let's do it. After cooling to room temperature, DDQ (90.8 mg, 0.4 mmol) and Toluene (1.0 mL) are added and allowed to react at room temperature for 10 minutes. After the reaction is completed, the solvent is removed using an evaporator. The column (Acetone: Hexane = 1: 30) was obtained to obtain the desired compound (E) -4- (3-bromostyryl) -2,3-diphenylselenophene (74.3 mg, 80%). ¹ H NMR (400 MHz, CDCl ₃ ) d 8.13 (s, 1H), 7.43-7.10 (m, 14H), 6.80 (d, J = 16.2 Hz, 1H), 6.69 (d, J = 16.2 Hz, 1H) .

(E) Preparation of -4- (3,4-dichlorostyryl) -2,3-diphenylselenophene

In dioxane solvent (1 mL) [Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( rac ) -BINAP (14.9 mg, 0.024 mmol), 4,5-diphenyl-1,2,3-selenadiazole ( 57.04 mg, 0.2 mmol), (E) -4- (buta-1,3-dien-1-yl) -1,2-dichlorobenzene (119.5 mg, 0.6 mmol) were added and then 130 ^° C. for 3 hours. React. After cooling to room temperature, DDQ (90.8 mg, 0.4 mmol) and Toluene (1.0 mL) are added and allowed to react at room temperature for 10 minutes. After the reaction is completed, the solvent is removed using an evaporator. The column (Acetone: Hexane = 1: 30) was obtained to obtain the desired compound (E) -4- (3,4-dichlorostyryl) -2,3-diphenylselenophene (71.8 mg, 79%). ¹ H NMR (400 MHz, CDCl ₃ ) d 8.13 (s, 1H), 7.35-7.08 (m, 13H), 6.75 (d, J = 16.2 Hz, 1H), 6.67 (d, J = 16.2 Hz, 1H) .

(E) Preparation of -4- (2-([1,1'-biphenyl] -4-yl) vinyl) -2,3-diphenylselenophene

In dioxane solvent (1 mL) [Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( rac ) -BINAP (14.9 mg, 0.024 mmol), 4,5-diphenyl-1,2,3-selenadiazole ( 57.04 mg, 0.2 mmol), (E) -4- (buta-1,3-dien-1-yl) -1,1'-biphenyl (123.8 mg, 0.6 mmol) was added and then added to 130 ^o C. Let time react. After cooling to room temperature, DDQ (90.8 mg, 0.4 mmol) and Toluene (1.0 mL) are added and allowed to react at room temperature for 10 minutes. After the reaction is completed, the solvent is removed using an evaporator. The column (Acetone: Hexane = 1: 30) was then run on the desired compound (E) -4- (2-([1,1'-biphenyl] -4-yl) vinyl) -2,3-diphenylselenophene (77.5). mg, 84%). ¹ H NMR (400 MHz, CDCl ₃ ) d 8.15 (s, 1H), 7.57 (d, J = 7.8 Hz, 2H), 7.51 (d, J = 8.3 Hz, 2H), 7.43-7.37 (m, 4H) , 7.33-7.30 (m, 4H), 7.23-7.17 (m, 7H), 6.94 (d, J = 16.2 Hz, 1H), 6.75 (d, J = 16.2 Hz, 1H).

Preparation of (E) -4- (2- (4,5-diphenylselenophen-3-yl) vinyl) benzonitrile

In dioxane solvent (1 mL) [Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( rac ) -BINAP (14.9 mg, 0.024 mmol), 4,5-diphenyl-1,2,3-selenadiazole ( 57.04 mg, 0.2 mmol) and (E) -4- (buta-1,3-dien-1-yl) benzonitrile (93.1 mg, 0.6 mmol) were added and reacted at 130 ^° C. for 3 hours. After cooling to room temperature, DDQ (90.8 mg, 0.4 mmol) and Toluene (1.0 mL) are added and allowed to react at room temperature for 10 minutes. After the reaction is completed, the solvent is removed using an evaporator. The column (Acetone: Hexane = 1: 30) can be obtained to obtain the desired compound (E) -4- (2- (4,5-diphenylselenophen-3-yl) vinyl) benzonitrile (73.3 mg, 92%). there was. ¹ H NMR (400 MHz, CDCl ₃ ) d 8.22 (s, 1H), 7.54 (d, J = 8.3 Hz, 2H), 7.37-7.32 (m, 5H), 7.19-7.15 (m, 7H), 6.87 ( d, J = 16.3 Hz, 1H), 6.80 (d, J = 16.2 Hz, 1H).

(E) Preparation of -4- (2- (naphthalen-2-yl) vinyl) -2,3-diphenylselenophene

In dioxane solvent (1 mL) [Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( rac ) -BINAP (14.9 mg, 0.024 mmol), 4,5-diphenyl-1,2,3-selenadiazole ( 57.04 mg, 0.2 mmol) and (E) -2- (buta-1,3-dien-1-yl) naphthalene (108.2 mg, 0.6 mmol) were added and then reacted at 130 ^° C. for 3 hours. After cooling to room temperature, DDQ (90.8 mg, 0.4 mmol) and Toluene (1.0 mL) are added and allowed to react at room temperature for 10 minutes. After the reaction is completed, the solvent is removed using an evaporator. The column (Acetone: Hexane = 1: 30) was then obtained to obtain the desired compound (E) -4- (2- (naphthalen-2-yl) vinyl) -2,3-diphenylselenophene (73.1 mg, 84%). Could. ¹ H NMR (400 MHz, CDCl ₃ ) d 8.14 (s, 1H), 7.74-7.67 (m, 4H), 7.46-7.16 (m, 13H), 7.05 (d, J = 16.2 Hz, 1H), 6.82 ( d, J = 16.2 Hz, 1H).

(E) Preparation of -2,3-diphenyl-4- (4- (trifluoromethyl) styryl) selenophene

In dioxane solvent (1 mL) [Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( rac ) -BINAP (14.9 mg, 0.024 mmol), 4,5-diphenyl-1,2,3-selenadiazole ( 57.04 mg, 0.2 mmol), (E) -1- (buta-1,3-dien-1-yl) -4- (trifluoromethyl) benzene (118.9 mg, 0.6 mmol) were added, followed by 3 to 130 ^o C. Let time react. After cooling to room temperature, DDQ (90.8 mg, 0.4 mmol) and Toluene (1.0 mL) are added and allowed to react at room temperature for 10 minutes. After the reaction is completed, the solvent is removed using an evaporator. The column (Acetone: Hexane = 1: 30) was obtained to obtain the desired compound (E) -2,3-diphenyl-4- (4- (trifluoromethyl) styryl) selenophene (49.9 mg, 55%). ¹ H NMR (400 MHz, CDCl ₃ ) d 8.18 (s, 1H), 7.50 (d, J = 8.2 Hz, 2H), 7.37 (d, J = 8.1 Hz, 2H), 7.34-7.31 (m, 3H) , 7.20-7.14 (m, 7H), 6.89 (d, J = 16.2 Hz, 1H), 6.78 (d, J = 16.2 Hz, 1H).

(E) Preparation of -2,3-bis (4-chlorophenyl) -4-styrylselenophene

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( rac ) -BINAP (14.9 mg, 0.024 mmol), 4,5-bis (4-chlorophenyl) -1,2 in dioxane solvent (1 mL) , 3-selenadiazole (70.82 mg, 0.2 mmol) and (E) -buta-1,3-dien-1-ylbenzene (78.1 mg, 0.6 mmol) were added and then reacted at 130 ^° C. for 3 hours. After cooling to room temperature, DDQ (90.8 mg, 0.4 mmol) and Toluene (1.0 mL) are added and allowed to react at room temperature for 10 minutes. After the reaction is completed, the solvent is removed using an evaporator. The column (Acetone: Hexane = 1: 30) was obtained to obtain the desired compound (E) -2,3-bis (4-chlorophenyl) -4-styrylselenophene (44.5 mg, 49%). ¹ H NMR (400 MHz, CDCl ₃ ) d 8.14 (s, 1H), 7.34-7.24 (m, 7H), 7.18 (d, J = 8.6 Hz, 2H), 7.11 (d, J = 8.5 Hz, 2H) , 7.06 (d, J = 8.6 Hz, 2H), 6.92 (d, J = 16.2 Hz, 1H), 6.64 (d, J = 16.2 Hz, 1H).

Preparation of (E) -2,3-dimethyl-4-styrylselenophene

In dioxane solvent (1 mL) [Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( rac ) -BINAP (14.9 mg, 0.024 mmol), 4,5-dimethyl-1,2,3-selenadiazole ( 32.2 mg, 0.2 mmol) and (E) -buta-1,3-dien-1-ylbenzene (78.1 mg, 0.6 mmol) were added and then reacted at 130 ^° C. for 3 hours. After cooling to room temperature, DDQ (90.8 mg, 0.4 mmol) and Toluene (1.0 mL) are added and allowed to react at room temperature for 10 minutes. After the reaction is completed, the solvent is removed using an evaporator. The column (Acetone: Hexane = 1: 30) was obtained to obtain the desired compound (E) -2,3-dimethyl-4-styrylselenophene (48.1 mg, 92%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.79 (s, 1H), 7.47 (d, J = 7.6 Hz, 2H), 7.33 (t, J = 7.6 Hz, 2H), 7.23 (t, J = 7.3 Hz , 1H), 6.97 (d, J = 16.1 Hz, 1H), 6.90 (d, J = 16.1 Hz, 1H), 2.45 (s, 3H), 2.12 (s, 3H).

(E) Preparation of -3-styryl-4,5,6,7-tetrahydrobenzo [b] selenophene

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( rac ) -BINAP (14.9 mg, 0.024 mmol), 4,5,6,7-tetrahydrobenzo [ d ] [1 in dioxane solvent (1 mL). , 2,3] selenadiazole (37.4 mg, 0.2 mmol) and (E) -buta-1,3-dien-1-ylbenzene (78.1 mg, 0.6 mmol) were added and then reacted at 130 ^° C. for 3 hours. After cooling to room temperature, DDQ (90.8 mg, 0.4 mmol) and Toluene (1.0 mL) are added and allowed to react at room temperature for 10 minutes. After the reaction is completed, the solvent is removed using an evaporator. The column (Acetone: Hexane = 1: 30) was obtained to obtain the desired compound (E) -3-styryl-4,5,6,7-tetrahydrobenzo [ b ] selenophene (48.8 mg, 85%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.82 (s, 1H), 7.46 (d, J = 7.2 Hz, 2H), 7.33 (t, J = 7.5 Hz, 2H), 7.25 (t, J = 3.6 Hz , 1H), 6.93 (dd, J = 17.5, 16.2 Hz, 1H), 2.86 (bs, 2H), 2.64 (s, 2H), 1.86-1.84 (m, 4H).

2. Synthesis according to Equation 79

Examples for the following selenium ring compounds synthesized according to Equation 79 will be described.

Preparation of 4,5-Diphenyl-3-propyl-1,2-selenazole

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-diphenyl-1,2,3- in Dioxane solvent (1 mL) Selenadiazole (57.04 mg, 0.2 mmol) and butyronitrile (0.17 mL, 2.0 mmol) were added, followed by reaction at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: DCM: Haxane = 1: 1: 20) was obtained to obtain the desired compound 4,5-diphenyl-3-propyl-1,2-selenazole (57.3 mg, 85%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.39-7.33 (m, 3H), 7.25-7.16 (m, 5H), 7.14-7.11 (m, 2H), 2.59 (t, J = 7.7 Hz, 2H), 1.67 ( sextet, J = 7.5 Hz, 2H), 0.88 (t, J = 7.4 Hz, 3H).

Preparation of 3-Methyl-4,5-diphenyl-1,2-selenazole

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-diphenyl-1,2,3- in Dioxane solvent (1 mL) After adding selenadiazole (57.04 mg, 0.2 mmol) and acetonitrile (0.10 mL, 2.0 mmol), the mixture was reacted at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: DCM: Haxane = 1: 1: 20) was then run on the desired compound, 3-methyl-4,5-diphenyl-1,2-selenazole. (34.5 g, 58%) was obtained. ¹ H NMR (400 MHz, CDCl ₃ ) d 7.39-7.33 (m, 3H), 7.26-7.12 (m, 7H), 2.31 (s, 3H).

Preparation of 3-Benzyl-4,5-diphenyl-1,2-selenazole

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-diphenyl-1,2,3- in Dioxane solvent (1 mL) Selenadiazole (57.04 mg, 0.2 mmol) and benzylcyanide (0.23 mL, 2.0 mmol) were added, followed by reaction at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: DCM: Haxane = 1: 1: 20) was obtained to obtain 3-benzyl-4,5-diphenyl-1,2-selenazole (59.8 g, 80%) as a desired compound. ¹ H NMR (400 MHz, CDCl ₃ ) d 7.33-7.25 (m, 3H), 7.22-7.10 (m, 8H), 7.05-7.02 (m, 2H), 7.00-6.98 (m, 2H), 3.98 (s, 2H ).

Preparation of 4,5-Diphenyl-3- (3-phenylpropyl) -1,2-selenazole

[Rh (COD) Cl] in Dioxane solvent (1 mL)₂ (4.93 mg, 0.01 mmol) and (S, S) -DIOP (12.0 mg, 0.024 mmol), 4,5-diphenyl-1,2,3-selenadiazole (57.04 mg, 0.2 mmol) and 4-phenylbutyronitrile (0.30 mL, 2.0 mmol) were added, followed by 100^oReact with C for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: DCM: Haxane = 1: 1: 20) was carried out to obtain the desired compound 4,5-diphenyl-3- (3-phenylpropyl) -1,2-selenazole. (49.0 g, 49%) was obtained. ^OneH NMR (400 MHz, CDCl₃)d7.34-7.32 (m, 3H), 7.25-7.18 (m, 5H), 7.15-7.11 (m, 5H), 7.08-7.06 (m, 2H), 2.66 (t,J = 7.7 Hz, 2H), 2.58 (t,J = 7.7 Hz, 2H), 1.96 (qui,J = 7.7 Hz, 2H).

Preparation of 4,5-Diphenyl-3- (thiophen-2-ylmethyl) -1,2-selenazole

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-diphenyl-1,2,3- in Dioxane solvent (1 mL) After adding selenadiazole (57.04 mg, 0.2 mmol) and 2-thiopheneacetonitrile (0.21 mL, 2.0 mmol), the mixture was reacted at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: DCM: Haxane = 1: 1: 20) was carried out to obtain the desired compound 4,5-diphenyl-3- (thiophen-2-ylmethyl) -1,2-selenazole. (68.2 g, 90%) was obtained. ¹ H NMR (400 MHz, CDCl ₃ ) d 7.34-7.32 (m, 3H), 7.25-7.18 (m, 3H), 7.14-7.09 (m, 5H), 6.84 (dd, J = 3.5 Hz, J = 5.1 Hz, 1H), 4.15 (s, 2H).

.

Preparation of (4,5-Diphenyl-1,2-selenazol-3-yl) (phenyl) methanone

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-diphenyl-1,2,3- in Dioxane solvent (1 mL) After adding selenadiazole (57.04 mg, 0.2 mmol) and benzylcyanide (0.24 mL, 2.0 mmol), the mixture was reacted at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: DCM: Haxane = 1: 1: 20) was added to the desired compound (4,5-diphenyl-1,2-selenazol-3-yl) (phenyl) methanone (78.6 g, 99%). Could get ¹ H NMR (400 MHz, CDCl ₃ ) d 7.98-7.75 (m, 2H), 7.60-7.56 (m, 1H), 7.47-7.43 (m, 2H), 7.34-7.26 (m, 3H), 7.23-7.19 (m , 5H), 7.15-7.12 (m, 2H).

Preparation of Ethyl 4,5-diphenyl-1,2-selenazole-3-carboxylate

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-diphenyl-1,2,3- in Dioxane solvent (1 mL) Selenadiazole (57.04 mg, 0.2 mmol) and ethylcyanoformate (0.20 mL, 2.0 mmol) were added, followed by reaction at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: DCM: Haxane = 1: 1: 20) was obtained to obtain the desired compound ethyl 4,5-diphenyl-1,2-selenazole-3-carboxylate (65.7 g, 93%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.34-7.31 (m, 3H), 7.30-7.22 (m, 3H), 7.21-7.18 (m, 2H), 7.15-7.13 (m, 2H), 4.23 (q, J = 7.1 Hz, 2H), 1.19 (t, J = 7.1 Hz, 3H).

Preparation of 3,4,5-Triphenyl-1,2-selenazole

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-diphenyl-1,2,3- in Dioxane solvent (1 mL) After adding selenadiazole (57.04 mg, 0.2 mmol) and benzonitrile (0.2 mL, 2.0 mmol), the mixture was reacted at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: DCM: Haxane = 1: 1: 20) was obtained to obtain a desired compound, 3,4,5-triphenyl-1,2-selenazole (20.2 g, 28%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.31-7.26 (m, 5H), 7.25-7.20 (m, 6H), 7.19-7.15 (m, 2H), 7.03-7.00 (m, 2H).

Preparation of 4,5-Diphenyl-3- (p-tolyl) -1,2-selenazole

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-diphenyl-1,2,3- in Dioxane solvent (1 mL) Selenadiazole (57.04 mg, 0.2 mmol) and 4-methylbenzonitrile (0.24 mL, 2.0 mmol) were added, followed by reaction at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: DCM: Haxane = 1: 1: 20) can be obtained to obtain the desired compound 4,5-diphenyl-3- ( p -tolyl) -1,2-selenazole (13.0 g, 18%). there was. ¹ H NMR (400 MHz, CDCl ₃ ) d 7.29-7.26 (m, 1H), 7.24-7.14 (m, 9H), 7.04-7.01 (m, 4H), 2.30 (s, 3H).

Preparation of 3- (4-Chlorophenyl) -4,5-diphenyl-1,2-selenazole

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-diphenyl-1,2,3- in Dioxane solvent (1 mL) After adding selenadiazole (57.04 mg, 0.2 mmol) and 4-chlorobenzonitrile (275.1 mg, 2.0 mmol), the mixture was reacted at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: DCM: Haxane = 1: 1: 20) can be obtained to obtain the desired compound, 3- (4-chlorophenyl) -4,5-diphenyl-1,2-selenazole (22.9 g, 30%). there was. ¹ H NMR (400 MHz, CDCl ₃ ) d 7.30-7.26 (m, 2H), 7.25-7.24 (m, 3H), 7.23-7.18 (m, 5H), 7.17-7.14 (m, 2H), 7.02-6.99 (m , 2H).

Preparation of Ethyl 4,5-di-p-tolyl-1,2-selenazole-3-carboxylate

In Dioxane solvent (1 mL) [Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-di- p- tolyl-1, 2,3-selenadiazole (62.65 mg, 0.2 mmol) and ethylcyanoformate (0.20 mL, 2.0 mmol) were added, followed by reaction at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: DCM: Haxane = 1: 1: 20) was obtained to obtain the desired compound ethyl 4,5-di-p-tolyl-1,2-selenazole-3-carboxylate (68.7 g, 90%). Could. ¹ H NMR (400 MHz, CDCl ₃ ) d 7.13 (d, J = 8.0 Hz, 2H), 7.09-7.07 (m, 2H), 7.04-7.02 (m, 4H), 4.24 (q, J = 7.1 Hz, 2H) , 2.35 (s, 3H), 2.29 (s, 3H), 1.22 (t, J = 7.1 Hz, 3H).

Preparation of Ethyl 4,5-bis (4-chlorophenyl) -1,2-selenazole-3-carboxylate

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-bis (4-chlorophenyl) -1 in dioxane solvent (1 mL) , 2,3-selenadiazole (70.82 mg, 0.2 mmol) and ethylcyanoformate (0.20 mL, 2.0 mmol) were added, followed by reaction at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: DCM: Haxane = 1: 1: 20) was added to the desired compound ethyl 4,5-bis (4-chlorophenyl) -1,2-selenazole-3-carboxylate (81.3 g, 96%). Could get ¹ H NMR (400 MHz, CDCl ₃ ) d 7.34-7.30 (m, 2H), 7.28-7.24 (m, 2H), 7.13-7.10 (m, 2H), 7.07-7.04 (m, 2H), 4.26 (d, J = 7.1 Hz, 2H), 1.25 (t, J = 7.1 Hz, 3H).

Preparation of 4,5-Dimethyl-3-propyl-1,2-selenazole

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-dimethyl-1,2,3- in Dioxane solvent (1 mL) Selenadiazole (32.21 mg, 0.2 mmol) and bytyronitrile (0.17 mL, 2.0 mmol) were added, followed by reaction at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: DCM: Haxane = 1: 1: 20) was obtained to obtain the desired compound 4,5-dimethyl-3-propyl-1,2-selenazole (23.2 g, 57%). ¹ H NMR (400 MHz, CDCl ₃ ) d 2.64 (t, J = 7.7 Hz, 2H), 2.49 (d, J = 0.4 Hz, 3H), 2.05 (d, J = 0.6 Hz, 3H), 1.75 (sextet, J = 7.5 Hz, 2H), 1.00 (t, J = 7.4 Hz, 3H).

Preparation of 3-Benzyl-4,5-dimethyl-1,2-selenazole

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-dimethyl-1,2,3- in Dioxane solvent (1 mL) After adding selenadiazole (32.21 mg, 0.2 mmol) and benzylcyanide (0.23 mL, 2.0 mmol), the mixture was reacted at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: DCM: Haxane = 1: 1: 20) was obtained to obtain 3-benzyl-4,5-dimethyl-1,2-selenazole (39.1 g, 78%) as a desired compound. ¹ H NMR (400 MHz, CDCl ₃ ) d 7.29-7.27 (m, 1H), 7.26-7.25 (m, 1H), 7.21-7.18 (m, 3H), 4.06 (s, 2H), 2.46 (d, J = 0.4 Hz, 3H), 1.94 (d, J = 0.5 Hz, 3H).

Preparation of Ethyl 4,5-dimethyl-1,2-selenazole-3-carboxylate

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-dimethyl-1,2,3- in Dioxane solvent (1 mL) Selenadiazole (32.21 mg, 0.2 mmol) and ethylcyanoformate (0.20 mL, 2.0 mmol) were added, followed by reaction at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: DCM: Haxane = 1: 1: 20) was obtained to obtain the desired compound, ethyl 4,5-dimethyl-1,2-selenazole-3-carboxylate (38.6 g, 838%). ¹ H NMR (400 MHz, CDCl ₃ ) d 4.41 (q, J = 7.1 Hz, 2H), 2.55 (s, 3H), 2.36 (s, 3H), 1.43 (t, J = 7.1 Hz, 3H).

Preparation of 4,5-Dimethyl-3-phenyl-1,2-selenazole

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-dimethyl-1,2,3- in Dioxane solvent (1 mL) After adding selenadiazole (32.21 mg, 0.2 mmol) and benzonitrile (0.20 mL, 2.0 mmol), the mixture was reacted at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: DCM: Haxane = 1: 1: 20) was obtained to obtain the desired compound 4,5-dimethyl-3-phenyl-1,2-selenazole (39.9 g, 84%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.53-7.50 (m, 2H), 7.46-7.38 (m, 3H), 2.56 (d, J = 0.4 Hz, 3H), 2.13 (d, J = 0.5 Hz, 3H) .

Preparation of 4,5-Dimethyl-3- ( p -tolyl) -1,2-selenazole

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-dimethyl-1,2,3- in Dioxane solvent (1 mL) Selenadiazole (32.21 mg, 0.2 mmol) and 4-methylbenzonitrile (0.24 mL, 2.0 mmol) were added, followed by reaction at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: DCM: Haxane = 1: 1: 20) can be obtained to obtain the desired compound 4,5-dimethyl-3- ( p -tolyl) -1,2-selenazole (42.6 g, 85%). there was. ¹ H NMR (400 MHz, CDCl ₃ ) d 7.43-7.41 (m, 2H), 7.25-7.23 (m, 2H), 2.55 (d, J = 0.4 Hz, 3H), 2.39 (s, 3H), 2.12 (d, J = 0.5 Hz, 3H).

Preparation of 3- (4-Chlorophenyl) -4,5-dimethyl-1,2-selenazole

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-dimethyl-1,2,3- in Dioxane solvent (1 mL) After adding selenadiazole (32.21 mg, 0.2 mmol) and 4-chlorobenzonitrile (275.1 mg, 2.0 mmol), the mixture was reacted at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: DCM: Haxane = 1: 1: 20) can be obtained to obtain 3- (4-chlorophenyl) -4,5-dimethyl-1,2-selenazole (44.8 g, 83%) as a desired compound. there was. ¹ H NMR (400 MHz, CDCl ₃ ) d 7.49-7.46 (m, 2H), 7.43-7.39 (m, 2H), 2.57 (d, J = 0.5 Hz, 3H), 2.12 (d, J = 0.6 Hz, 3H) .

Preparation of 3-Methyl-4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazole

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 4,5,6,7-tetrahydrobenzo [ d ] in Dioxane solvent (1 mL) [1,2,3] selenadiazole (37.42 mg, 0.2 mmol) and acetonitrile (0.10 mL, 2.0 mmol) were added, followed by reaction at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: DCM: Haxane = 1: 1: 20) was subjected to 3-methyl-4,5,6,7-tetrahydro-benzo [ d ] [1,2] selenazole (14.1 g, 35). %) Could be obtained. ¹ H NMR (400 MHz, CDCl ₃ ) d 2.91-2.90 (m, 2H), 2.53-2.50 (s, 3H), 1.83-1.81 (m, 4H), 9.04 (s, 1H).

Preparation of 3-Propyl-4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazole

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 4,5,6,7-tetrahydrobenzo [ d ] in Dioxane solvent (1 mL) [1,2,3] selenadiazole (37.42 mg, 0.2 mmol) and butyronitrile (0.17 mL, 2.0 mmol) were added, followed by reaction at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: DCM: Haxane = 1: 1: 20) was then subjected to 3-propyl-4,5,6,7-tetrahydro-benzo [ d ] [1,2] selenazole (30.8 g, 68). %) Could be obtained. ¹ H NMR (400 MHz, CDCl ₃ ) d 2.92-2.89 (m, 2H), 2.60 (t, J = 7.7 Hz, 2H), 2.55-2.52 (m, 2H), 1.85-1.71 (m, 6H), 0.99 ( t, J = 7.4 Hz, 3H).

Preparation of 3-Benzyl-4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazole

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 4,5,6,7-tetrahydrobenzo [ d ] in Dioxane solvent (1 mL) [1,2,3] selenadiazole (37.42 mg, 0.2 mmol) and benzylcyanide (0.23 mL, 2.0 mmol) were added, followed by reaction at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. Then proceed to the column (Ether: DCM: Haxane = 1: 1: 20) to the desired compound 3-benzyl-4,5,6,7-tetrahydro-benzo [ d ] [1,2] selenazole (43.3 g, 78 %) Could be obtained. ¹ H NMR (400 MHz, CDCl ₃ ) d 7.29-7.25 (m, 2H), 7.21-7.18 (m, 3H), 4.02 (s, 2H), 2.89 (t, J = 6.0 Hz, 2H), 2.41 (t, J = 6.0 Hz, 2H), 1.81-1.70 (m, 4H).

Preparation of 3- (3-Phenylpropyl) -4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazole

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 4,5,6,7-tetrahydrobenzo [ d ] in Dioxane solvent (1 mL) [1,2,3] selenadiazole (37.42 mg, 0.2 mmol) and 4-phenylbutyronitrile (0.30 mL, 2.0 mmol) were added and reacted at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: DCM: Haxane = 1: 1: 20) was then subjected to 3- (3-phenylpropyl) -4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazole (51.3 g) as the desired compound. , 85%). ¹ H NMR (400 MHz, CDCl ₃ ) δ 7.28-7.25 (m, 2H), 7.20-7.15 (m, 3H), 2.91-2.88 (m, 2H), 2.71 (t, J = 7.6 Hz, 2H), 2.64 ( t, J = 7.7 Hz, 2H), 2.49-2.45 (m, 2H), 2.07 (qui, J = 7.7 Hz, 2H), 1.84-1.74 (m, 4H).

Preparation of 3- (Thiophen-2-ylmethyl) -4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazole

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 4,5,6,7-tetrahydrobenzo [ d ] in Dioxane solvent (1 mL) [1,2,3] selenadiazole (37.42 mg, 0.2 mmol) and 2-thiopheneacetonitrile (0.21 mL, 2.0 mmol) were added, followed by reaction at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. Then, the column (Ether: DCM: Haxane = 1: 1: 20) was carried out to obtain 3- (thiophen-2-ylmethyl) -4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazole ( 52.4 g, 93%). ¹ H NMR (400 MHz, CDCl ₃ ) δ 7.15 (dd, J = 5.1 Hz, J = 1.2, Hz, 1H), 6.91 (dd, J = 5.1 Hz, J = 3.5 Hz, 1H), 6.82-6.80 (m, 1H), 4.19 (d, J = 0.8 Hz, 2H), 2.92-2.88 (m, 2H), 2.52-2.48 (m, 2H), 1.84-1.73 (m, 4H).

Preparation of Phenyl (4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazol-3-yl) methanone

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 4,5,6,7-tetrahydrobenzo [ d ] in Dioxane solvent (1 mL) [1,2,3] selenadiazole (37.42 mg, 0.2 mmol) and benzoylcyanide (0.24 mL, 2.0 mmol) were added, followed by reaction at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: DCM: Haxane = 1: 1: 20) was then run to obtain the desired compound, phenyl (4,5,6,7-tetrahydro-benzo [ d ] [1,2] selenazol-3-yl) methanone ( 46.1 g, 80%). ¹ H NMR (400 MHz, CDCl ₃ ) d 8.04 (d, J = 7.4 Hz, 2H), 7.58 (t, J = 7.4 Hz, 1H), 7.46 (t, J = 7.7 Hz, 2H), 3.00-2.97 (m , 2H), 2.88-2.85 (m, 2H), 1.91-1.85 (m, 2H), 1.82-1.76 (m, 2H).

Preparation of Ethyl 4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazole-3-carboxylate

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 4,5,6,7-tetrahydrobenzo [ d ] in Dioxane solvent (1 mL) [1,2,3] selenadiazole (37.42 mg, 0.2 mmol) and ethylcyanoformate (0.20 mL, 2.0 mmol) were added, followed by reaction at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: DCM: Haxane = 1: 1: 20) was subjected to ethyl 4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazole-3-carboxylate (48.0 g, 93%). Could get. ¹ H NMR (400 MHz, CDCl ₃ ) d 4.40 (q, J = 7.1 Hz, 2H), 2.98-2.95 (m, 4H), 1.89-1.78 (m, 4H), 1.43 (t, J = 7.1 Hz, 3H) .

Preparation of 3-Phenyl-4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazole

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 4,5,6,7-tetrahydrobenzo [ d ] in Dioxane solvent (1 mL) [1,2,3] selenadiazole (37.42 mg, 0.2 mmol) and benzonitrile (0.20 mL, 2.0 mmol) were added, followed by reaction at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: DCM: Haxane = 1: 1: 20) was subjected to 3-phenyl-4,5,6,7-tetrahydro-benzo [ d ] [1,2] selenazole (48.6 g, 88). %) Could be obtained. ¹ H NMR (400 MHz, CDCl ₃ ) d 7.59-7.56 (m, 2H), 7.45-7.38 (m, 3H), 3.00 (t, J = 6.2 Hz, 2H), 2.66 (t, J = 6.1 Hz, 2H) , 1.93-1.87 (m, 2H), 1.80-1.74 (m, 2H).

Preparation of 3- ( o -Tolyl) -4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazole

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 4,5,6,7-tetrahydrobenzo [ d ] in Dioxane solvent (1 mL) [1,2,3] selenadiazole (37.42 mg, 0.2 mmol) and 2-methylbenzonitrile (0.24 mL, 2.0 mmol) were added, followed by reaction at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: DCM: Haxane = 1: 1: 20) was subjected to 3- ( o -tolyl) -4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazole (48.6 g). , 88%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.31-7.15 (m, 4H), 3.00 (t, J = 6.2 Hz, 2H), 2.31 (t, J = 6.1 Hz, 2H), 2.15 (s, 3H), 1.90 -1.84 (m, 2 H), 1.76-1.70 (m, 2 H).

Preparation of 3- ( m -Tolyl) -4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazole

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 4,5,6,7-tetrahydrobenzo [ d ] in Dioxane solvent (1 mL) [1,2,3] selenadiazole (37.42 mg, 0.2 mmol) and 3-methylbenzonitrile (0.24 mL, 2.0 mmol) were added and reacted at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. Then proceed to the column (Ether: DCM: Haxane = 1: 1: 20) to the desired compound 3- ( m -tolyl) -4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazole (52.5 g , 95%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.42 (s, 1H), 7.36-7.29 (m, 2H), 7.22 (d, J = 7.3 Hz, 1H), 3.00 (t, J = 6.2 Hz, 2H), 2.66 (t, J = 6.1 Hz, 2H), 1.92-11.86 (m, 2H), 1.79-1.74 (m, 2H).

Preparation of 3- ( p -Tolyl) -4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazole

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 4,5,6,7-tetrahydrobenzo [ d ] in Dioxane solvent (1 mL) [1,2,3] selenadiazole (37.42 mg, 0.2 mmol) and 4-methylbenzonitrile (0.24 mL, 2.0 mmol) were added, followed by reaction at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. Then proceed to the column (Ether: DCM: Haxane = 1: 1: 20) to the desired compound 3- ( p -tolyl) -4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazole (82.9 g , 95%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.48 (d, J = 8.0 Hz, 2H), 7.23 (d, J = 7.8 Hz, 2H), 2.99 (t, J = 6.2 Hz, 2H), 2.66 (t, J = 6.0 Hz, 2H), 2.38 (s, 3H), 1.90-1.86 (m, 2H), 1.79-1.75 (m, 2H).

Preparation of 3- (4-Fluorophenyl) -4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazole

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 4,5,6,7-tetrahydrobenzo [ d ] in Dioxane solvent (1 mL) [1,2,3] selenadiazole (37.42 mg, 0.2 mmol) and 4-fluorolbenzonitrile (242.2 mg, 2.0 mmol) were added and reacted at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: DCM: Haxane = 1: 1: 20) was subjected to 3- (4-fluorophenyl) -4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazole (49.0 g). , 87%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.59-7.55 (m, 2H), 7.13-7.09 (m, 2H), 3.00 (t, J = 6.2 Hz, 2H), 2.64 (t, J = 6.1 Hz, 2H) , 1.93-1.87 (m, 2H), 1.81-1.75 (m, 2H).

Preparation of 3- (3-Chlorophenyl) -4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazole

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 4,5,6,7-tetrahydrobenzo [ d ] in Dioxane solvent (1 mL) [1,2,3] selenadiazole (37.42 mg, 0.2 mmol) and 3-chlorolbenzonitrile (275.1 mg, 2.0 mmol) were added and reacted at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: DCM: Haxane = 1: 1: 20) was subjected to 3- (3-chlorophenyl) -4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazole (59.1 g). , 99%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.59-7.58 (m, 1H), 7.48-7.45 (m, 1H), 7.39-7.32 (s, 2H), 2.99 (t, J = 6.2 Hz, 2H), 2.65 ( t, J = 6.1 Hz, 2H), 1.92-1.86 (m, 2H), 1.80-1.74 (m, 2H).

Preparation of 3- (4-Chlorophenyl) -4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazole

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 4,5,6,7-tetrahydrobenzo [ d ] in Dioxane solvent (1 mL) [1,2,3] selenadiazole (37.42 mg, 0.2 mmol) and 4-chlorolbenzonitrile (275.1 mg, 2.0 mmol) were added and reacted at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: DCM: Haxane = 1: 1: 20) was then run to obtain the desired compound, 3- (4-chlorophenyl) -4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazole (54.2 g , 92%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.54-7.51 (m, 2H), 7.41-7.39 (m, 2H), 3.00 (t, J = 6.2 Hz, 2H), 2.64 (t, J = 6.0 Hz, 2H) , 1.92-1.87 (m, 2H), 1.80-1.75 (m, 2H)

Preparation of 3- (4-Bromophenyl) -4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazole

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 4,5,6,7-tetrahydrobenzo [ d ] in Dioxane solvent (1 mL) [1,2,3] selenadiazole (37.42 mg, 0.2 mmol) and 4-bromobenzonitrile (364.0 mg, 2.0 mmol) were added and allowed to react at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: DCM: Haxane = 1: 1: 20) was subjected to 3- (4-bromophenyl) -4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazole (63.9 g). , 94%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.57-7.55 (m, 2H), 7.48-7.46 (m, 2H), 3.00 (t, J = 6.2 Hz, 2H), 2.64 (t, J = 6.0 Hz, 2H) , 1.93-1.87 (m, 2H), 1.80-1.75 (m, 2H).

Preparation of 1- (4- (4,5,6,7-Tetrahydrobenzo [ d ] [1,2] selenazol-3-yl) phenyl) ethanone

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 4,5,6,7-tetrahydrobenzo [ d ] in Dioxane solvent (1 mL) [1,2,3] selenadiazole (37.42 mg, 0.2 mmol) and 4-acetylbenzonitrile (290.3 mg, 2.0 mmol) were added, followed by reaction at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: DCM: Haxane = 1: 1: 20) was carried out to obtain the desired compound 1- (4- (4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazol-3-yl) phenyl) ethanone (55.4 g, 92%) was obtained. ¹ H NMR (400 MHz, CDCl ₃ ) d 8.02 (d, J = 8.3 Hz, 2H), 7.70 (d, J = 8.2 Hz, 2H), 3.01 (t, J = 6.1 Hz, 2H), 2.67 (t, J = 6.0 Hz, 2H), 2.64 (s, 3H), 1.92-1.88 (m, 2H), 1.81-1.75 (m, 2H).

Preparation of 4- (4,5,6,7-Tetrahydrobenzo [ d ] [1,2] selenazol-3-yl) benzonitrile

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 4,5,6,7-tetrahydrobenzo [ d ] in Dioxane solvent (1 mL) [1,2,3] selenadiazole (37.42 mg, 0.2 mmol) and terephthalonitrile (256.3 mg, 2.0 mmol) were added, followed by reaction at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: DCM: Haxane = 1: 1: 20) was then run to obtain the desired compound, 4- (4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazol-3-yl) benzonitrile (53.7). g, 94%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.72 (s, 4H), 3.02 (t, J = 6.2 Hz, 2H), 2.66 (t, J = 6.0 Hz, 2H), 1.94-1.88 (m, 2H), 1.82 -1.76 (m, 2 H).

Preparation of 3- (4-Nitrophenyl) -4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazole

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 4,5,6,7-tetrahydrobenzo [ d ] in Dioxane solvent (1 mL) [1,2,3] selenadiazole (37.42 mg, 0.2 mmol) and 4-nitrobenzonitrile (296.2 mg, 2.0 mmol) were added, followed by reaction at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: DCM: Haxane = 1: 1: 20) was subjected to 3- (4-nitrophenyl) -4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazole (56.9 g). , 93%). ¹ H NMR (400 MHz, CDCl ₃ ) d 8.29 (d, J = 8.8 Hz, 2H), 7.78 (d, J = 8.8 Hz, 2H), 3.03 (t, J = 6.2 Hz, 2H), 2.68 (t, J = 6.0 Hz, 2H), 1.95-1.90 (m, 2H), 1.84-1.78 (m, 2H).

Preparation of 3- (Pyridin-2-yl) -4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazole

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 4,5,6,7-tetrahydrobenzo [ d ] in Dioxane solvent (1 mL) [1,2,3] selenadiazole (37.42 mg, 0.2 mmol) and picolinonitrile (0.20 mL, 2.0 mmol) were added, followed by reaction at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: DCM: Haxane = 1: 1: 20) was then subjected to 3- (pyridin-2-yl) -4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazole ( 50.0 mg, 95%) was obtained. ¹ H NMR (400 MHz, CDCl ₃ ) d 8.64-8.63 (m, 1H), 7.90 (d, J = 7.9 Hz, 1H), 7.76 (td, J = 11.6 Hz, J = 1.7 Hz, 1H), 7.31-7.28 (m, 1H), 3.01-2.95 (m, 7H), 1.92-1.86 (m, 2H), 1.82-1.76 (m, 2H).

Preparation of 1-Phenyl-4,5-dihydronaphtho [1,2- d ] [1,2] selenazole

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-dihydronaphtho [1,2- d ] in Dioxane solvent (1 mL) [1,2,3] selenadiazole (47.43 mg, 0.2 mmol) and benzonitrile (0.20 mL, 2.0 mmol) were added, followed by reaction at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: DCM: Haxane = 1: 1: 20) was then run to obtain the desired compound, 1-phenyl-4,5-dihydronaphtho [1,2- d ] [1,2] selenazole (30.2 g, 49%). Could get ¹ H NMR (400 MHz, CDCl ₃ ) d 7.55-7.52 (m, 2H), 7.46-7.39 (m, 3H), 7.28-7.26 (m, 1H), 7.12 (td, J = 11.2 Hz, J = 1.3 Hz, 1H), 6.99-6.94 (m, 1H), 6.85-6.83 (m, 1H), 3.12-3.08 (m, 2H), 3.04-3.00 (m, 2H),

Preparation of 1- ( p -Tolyl) -4,5-dihydronaphtho [1,2- d ] [1,2] selenazole

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-dihydronaphtho [1,2- d ] in Dioxane solvent (1 mL) [1,2,3] selenadiazole (47.43 mg, 0.2 mmol) and 4-methylbenzonitrile (0.24 mL, 2.0 mmol) were added, followed by reaction at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. Then proceed to the column (Ether: DCM: Haxane = 1: 1: 20) to the desired compound 1- ( p -tolyl) -4,5-dihydronaphtho [1,2- d ] [1,2] selenazole (26.6 g , 41%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.34-7.41 (m, 2H), 7.27-7.25 (m, 1H), 7.22-7.20 (m, 2H), 7.11 (td, J = 11.1, J = 1.3 Hz, 1H ), 7.00-6.96 (m, 1H), 6.90 (dd, J = 7.8 Hz, J = 1.0 Hz, 1H), 3.09-3.05 (m, 2H), 3.02-2.98 (m, 2H), 2.41 (s, 3H).

Preparation of 1- (4-Chlorophenyl) -4,5-dihydronaphtho [1,2- d ] [1,2] selenazole

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 4,5-dihydronaphtho [1,2- d ] in Dioxane solvent (1 mL) [1,2,3] selenadiazole (47.43 mg, 0.2 mmol) and 4-chlorolbenzonitrile (275.14 mg, 2.0 mmol) were added, followed by reaction at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: DCM: Haxane = 1: 1: 20) was then run to obtain the desired compound 1- (4-chlorophenyl) -4,5-dihydronaphtho [1,2- d ] [1,2] selenazole (32.7 g , 48%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.50-7.47 (m, 2H), 7.41-7.37 (m, 2H), 7.28 (dd, J = 7.5 Hz, J = 0.7 Hz, 1H), 7.14 (td, J = 11.2 Hz, J = 1.3 Hz, 1H), 7.03-7.00 (m, 1H), 6.86 (dd, J = 7.8 Hz, J = 0.9 Hz, 1H), 3.10-3.06 (m, 2H), 3.03-3.00 ( m, 2H).

Preparation of 1-Phenyl-4 H -chromeno [4,3 - d ] [1,2] selenazole

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 4 H -chromeno [4,3- d ] [in Dioxane solvent (1 mL) [ 1,2,3] selenadiazole (47.43 mg, 0.2 mmol) and benzonitrile (0.20 mL, 2.0 mmol) are added and reacted at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: DCM: Haxane = 1: 1: 20) was added to the desired compound 1-phenyl-4 H -chromeno [4,3- d ] [1,2] selenazole (45.4 g, 73%). Could get ¹ H NMR (400 MHz, CDCl ₃ ) d 7.53-7.42 (m, 5H), 7.17-7.12 (m, 1H), 7.03 (dd, J = 8.1 Hz, J = 1.0 Hz, 1H), 6.85 (dd, J = 7.8 Hz, J = 1.5 Hz, 1H), 6.77-6.73 (m, 1H), 5.37 (s, 2H)

Preparation of 1- ( p -Tolyl) -4 H -chromeno [4,3- d ] [1,2] selenazole

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 4 H -chromeno [4,3- d ] [in Dioxane solvent (1 mL) [ 1,2,3] selenadiazole (47.43 mg, 0.2 mmol) and 4-methylbenzonitrile (0.24 mL, 2.0 mmol) were added, followed by reaction at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: DCM: Haxane = 1: 1: 20) was then subjected to the desired compound 1- ( p -tolyl) -4 H -chromeno [4,3- d ] [1,2] selenazole (41.8 g, 65%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.41 (d, J = 8.0 Hz, 2H), 7.24 (d, J = 7.3 Hz, 2H), 7.16-7.12 (m, 1H), 7.03 (dd, J = 8.1 Hz , J = 1.0 Hz, 1H), 6.92 (dd, J = 7.8 Hz, J = 1.5 Hz, 1H), 6.78-6.74 (m, 1H), 5.36 (s, 2H), 2.43 (s, 3H).

Preparation of 1- (4-Chlorophenyl) -4 H -chromeno [4,3- d ] [1,2] selenazole

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 4 H -chromeno [4,3- d ] [in Dioxane solvent (1 mL) [ 1,2,3] selenadiazole (47.43 mg, 0.2 mmol) and 4-chlorobenzonitrile (275.14 mg, 2.0 mmol) are added and reacted at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. And column (Ether: DCM: Haxane = 1 : 1: 20) proceed to the desired compound, 1- (4-chlorophenyl) -4 the H -chromeno [4,3- d] [1,2 ] selenazole (48.8 g, 70%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.49-7.46 (m, 2H), 7.44-7.41 (m, 2H), 7.19-7.15 (m, 1H), 7.04 (dd, J = 8.1 Hz, J = 1.1 Hz, 1H), 6.87 (dd, J = 7.8 Hz, J = 1.6 Hz, 1H), 6.82-6.77 (m, 1H), 5.36 (s, 2H).

Preparation of Ethyl 5-methyl-4-phenyl-1,2-selenazole-3-carboxylate

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 5-methyl-4-phenyl-1,2, in Dioxane solvent (1 mL) 3-selenadiazole (44.63 mg, 0.2 mmol) and ethylcyanoformate (0.20 mL, 2.0 mmol) were added, followed by reaction at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: DCM: Haxane = 1: 1: 20) was obtained to obtain the desired compound ethyl 5-methyl-4-phenyl-1,2-selenazole-3-carboxylate (34.6 g, 59%). . ¹ H NMR (400 MHz, CDCl ₃ ) d 7.45-7.37 (m, 3H), 7.21-7.19 (m, 2H), 4.20 (q, J = 7.1 Hz, 2H), 2.46 (s, 3H), 1.18 (t, J = 7.1 Hz, 3H).

Preparation of Ethyl 4-methyl-5-phenyl-1,2-selenazole-3-carboxylate

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 5-methyl-4-phenyl-1,2, in Dioxane solvent (1 mL) 3-selenadiazole (44.63 mg, 0.2 mmol) and ethylcyanoformate (0.20 mL, 2.0 mmol) were added, followed by reaction at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: DCM: Haxane = 1: 1: 20) was obtained to obtain the desired compound, ethyl 4-methyl-5-phenyl-1,2-selenazole-3-carboxylate (18.4 g, 31%). . ¹ H NMR (400 MHz, CDCl ₃ ) d 7.50-7.38 (m, 5H), 4.45 (q, J = 7.1 Hz, 2H), 2.45 (s, 3H), 1.46 (t, J = 7.1 Hz, 3H).

Preparation of Ethyl 5- (4-methoxyphenyl) -4-phenyl-1,2-selenazole-3-carboxylate

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 5- (4-methoxyphenyl) -4-phenyl- in Dioxane solvent (1 mL). 1,2,3-selenadiazole (63.05 mg, 0.2 mmol) and ethylcyanoformate (0.20 mL, 2.0 mmol) were added, followed by reaction at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. Then, the column (Ether: DCM: Haxane = 1: 1: 20) was carried out to obtain the desired compound, ethyl 5- (4-methoxyphenyl) -4-phenyl-1,2-selenazole-3-carboxylate (41.0 g, 53%). Could get ¹ H NMR (400 MHz, CDCl ₃ ) d 7.34-7.32 (m, 3H), 7.21-7.19 (m, 2H), 7.08-7.04 (m, 2H), 6.77-6.74 (m, 2H), 4.22 (q, J = 7.1 Hz, 2H), 3.67 (s, 3H), 1.18 (t, J = 7.1 Hz, 3H).

Preparation of Ethyl 4- (4-methoxyphenyl) -5-phenyl-1,2-selenazole-3-carboxylate

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 4- (4-methoxyphenyl) -5-phenyl- in Dioxane solvent (1 mL). 1,2,3-selenadiazole (63.05 mg, 0.2 mmol) and ethylcyanoformate (0.20 mL, 2.0 mmol) were added, followed by reaction at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. Then proceed with the column (Ether: DCM: Haxane = 1: 1: 20) to the desired compound ethyl 4- (4-methoxyphenyl) -5-phenyl-1,2-selenazole-3-carboxylate (32.5 g, 42%) Could get ¹ H NMR (400 MHz, CDCl ₃ ) d 7.29-7.23 (m, 3H), 7.16-7.10 (m, 4H), 6.85 (d, J = 8.7 Hz, 2H), 4.26 (q, J = 7.1 Hz, 2H) , 3.81 (s, 3 H), 1.24 (t, J = 7.1 Hz, 3 H).

Preparation of Ethyl 5- (4-chlorophenyl) -4-phenyl-1,2-selenazole-3-carboxylate

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 5- (4-chlorophenyl) -4-phenyl- in Dioxane solvent (1 mL). 1,2,3-selenadiazole (63.93 mg, 0.2 mmol) and ethylcyanoformate (0.20 mL, 2.0 mmol) were added and reacted at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: DCM: Haxane = 1: 1: 20) was then subjected to ethyl 5- (4-chloro-phenyl) -4-phenyl-1,2-selenazole-3-carboxylate (76.0 g, 98). %) Could be obtained. ¹ H NMR (400 MHz, CDCl ₃ ) d 7.34-7.25 (m, 8H), 7.22 (d, J = 8.5 Hz, 2H), 7.19-7.12 (m, 6H), 7.06 (d, J = 8.5 Hz, 2H) , 4.29-4.20 (m, 4H), 1.24 (t, J = 7.1 Hz, 3H), 1.18 (t, J = 7.1 Hz, 3H)

Preparation of Ethyl 4- (4-chlorophenyl) -5-phenyl-1,2-selenazole-3-carboxylate

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 4- (4-chlorophenyl) -5-phenyl- in dioxane solvent (1 mL). 1,2,3-selenadiazole (63.93 mg, 0.2 mmol) and ethylcyanoformate (0.20 mL, 2.0 mmol) were added and reacted at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: DCM: Haxane = 1: 1: 20) was carried out to obtain the desired compound, ethyl 4- (4-chlorophenyl) -5-phenyl-1,2-selenazole-3-carboxylate (77.0 g, 99%). Could get ¹ H NMR (400 MHz, CDCl ₃ ) d 7.35-7.25 (m, 24H), 7.23-7.21 (m, 2H), 7.19-7.11 (m, 18H), 7.07-7.05 (m, 2H), 4.29-4.20 (m , 10H), 1.24 (t, J = 7.1 Hz, 12H), 1.18 (t, J = 7.1 Hz, 3H).

Preparation of Ethyl 4- (benzo [ d ] [1,3] dioxol-5-yl) -5-phenyl-1,2-selenazole-3-carboxylate

[Rh (COD) Cl] ₂ (4.93 mg, 0.01 mmol) and ( S, S ) -DIOP (12.0 mg, 0.024 mmol), 4- (benzo [ d ] [1,3] in dioxane solvent (1 mL) After adding dioxol-5-yl) -5-phenyl-1,2,3-selenadiazole (65.85 mg, 0.2 mmol) and ethylcyanoformate (0.20 mL, 2.0 mmol), the mixture was reacted at 100 ^° C. for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. Then, the column (Ethyl acetate: Haxane = 1: 10) was processed to obtain the desired compound, ethyl 4- (benzo [ d ] [1,3] dioxol-5-yl) -5-phenyl-1,2-selenazole-3- Carboxylate (32.9 g, 41%) was obtained. ¹ H NMR (400 MHz, CDCl ₃ ) d 7.35-7.32 (m, 3.5H), 7.31-7.25 (m, 4.5H), 7.21-7.16 (m, 4.7H), 6.77-6.75 (m, 1.5H), 6.70 -6.63 (m, 4.6H), 6.53 (s, 1H), 5.97 (s, 2.8H), 5.92 (s, 2H), 4.28 (q, J = 7.1 Hz, 2.8H), 4.21 (q, J = 7.1 Hz, 2H), 1.27 (t, J = 7.1 Hz, 5.4H), 1.18 (t, J = 7.1 Hz, 3H).

Preparation of N- (2- (4,5,6,7-Tetrahydrobenzo [ d ] [1,2] selenazol-3-yl) phenyl) benzamide

[Cp * IrCl ₂ ] ₂ (6.39 mg, 0.008 mmol), AgSbF ₆ (11.0 mg, 0.032 mmol), 3-phenyl-4,5,6,7-tetrahydrobenzo [ d ] [1 in DCE solvent (1 mL) , 2] selenazole (78.67 mg, 0.3 mmol) and 3-phenyl-1,4,2-dioxazol-5-one (32.63 mg, 0.2 mmol) were added and then reacted at 80 ^° C. for 1 hour. After the reaction is completed, the solvent is removed using an evaporator. The column (Ethyl acetate: Haxane = 1: 10) was carried out to obtain the desired compound N- (2- (4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazol-3-yl) phenyl) benzamide (66.5 mg, 87%) was obtained. ¹ H NMR (400 MHz, CDCl ₃ ) d 10.98 (s, 1H), 8.63-8.60 (m, 1H), 7.90-7.87 (m, 2H), 7.53-7.40 (m, 5H), 7.20-7.15 (m, 1H ), 3.03 (t, J = 6.3 Hz, 2H), 2.65 (t, J = 6.0 Hz, 2H), 1.94-1.88 (m, 2H), 1.78-1.72 (m, 2H).

Preparation of 3- Methyl - N- (2- (4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazol-3-yl) phenyl) benzamide

[Cp * IrCl ₂ ] ₂ (6.39 mg, 0.008 mmol), AgSbF ₆ (11.0 mg, 0.032 mmol), 3-phenyl-4,5,6,7-tetrahydrobenzo [ d ] [1 in DCE solvent (1 mL) , 2] selenazole (78.67 mg, 0.3 mmol) and 3- ( m -tolyl) -1,4,2-dioxazol-5-one (35.4 mg, 0.2 mmol) were added and then reacted at 80 ^o C for 1 hour. Let's do it. After the reaction is completed, the solvent is removed using an evaporator. Then, the column (Ether: DCM: Haxane = 1: 1: 20) was subjected to 3-methyl- N- (2- (4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazol- 3-yl) phenyl) benzamide (59.4 g, 75%) was obtained. ¹ H NMR (400 MHz, CDCl ₃ ) d 10.92 (s, 1H), 8.64-8.62 (m, 1H), 7.69-7.66 (m, 2H), 7.47-7.45 (m, 1H), 7.41 (dd, J = 7.8 Hz, J = 1.4 Hz, 1H), 7.36-7.30 (m, 2H), 7.19-7.15 (m, 1H), 3.02 (t, J = 6.3 Hz, 2H), 2.64 (t, J = 6.0 Hz, 2H ), 2.42 (s, 3H), 1.93-1.87 (m, 2H), 1.77-1.71 (m, 2H).

Preparation of 3-Chloro- N- (2- (4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazol-3-yl) phenyl) benzamide

[Cp * IrCl ₂ ] ₂ (6.39 mg, 0.008 mmol), AgSbF ₆ (11.0 mg, 0.032 mmol), 3-phenyl-4,5,6,7-tetrahydrobenzo [ d ] [1 in DCE solvent (1 mL) , 2] selenazole (78.67 mg, 0.3 mmol) and 3- (3-chlorophenyl) -1,4,2-dioxazol-5-one (36.5 mg, 0.2 mmol) were added and then reacted at 80 ^o C for 1 hour. Let's do it. After the reaction is completed, the solvent is removed using an evaporator. Then, the column (Ethyl acetate: Haxane = 1: 10) was subjected to 3-chloro- N- (2- (4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazol-3-yl ) phenyl) -benzamide (68.6 g, 83%) was obtained. ¹ H NMR (400 MHz, CDCl ₃ ) d 11.13 (s, 1H), 8.61-8.60 (m, 1H), 7.88 (t, J = 1.8 Hz, 1H), 7.76 (dt, J = 7.7 Hz, J = 1.4 Hz , 1H), 7.49-7.38 (m, 4H), 7.21-7.17 (m, 1H), 3.04 (t, J = 6.3 Hz, 1H), 2.66 (t, J = 6.0 Hz, 2H), 1.94-1.88 ( m, 2H), 1.78-1.72 (m, 2H).

Preparation of ( E ) -Ethyl 3- (2- (4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazol-3-yl) phenyl) acrylate

[Cp * RhCl ₂ ] ₂ (3.09 mg, 0.005 mmol) and Cu (OAc) ₂ (36.3 mg, 0.2 mmol), 3-phenyl-4,5,6,7-tetrahydrobenzo [ d in DCE solvent (2 mL). ] [1,2] selenazole (52.45 mg, 0.2 mmol) and ethyl acrylate (0.026 mL, 0.24 mmol) are added and reacted at 90 ^o C for 1 hour. After the reaction is completed, the solvent is removed using an evaporator. Then, the column (Tetrahydrofuran: Haxane = 1: 30) was carried out to obtain the desired compound ( E ) -ethyl 3- (2- (4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazol-3-yl ) phenyl) acrylate (64.0 mg, 85%) was obtained. ¹ H NMR (400 MHz, CDCl ₃ ) d 7.74-7.70 (m, 1H), 7.52 (d, J = 16.0 Hz, 1H), 7.45-7.40 (m, 2H), 7.34-7.30 (m, 1H), 6.33 ( d, J = 16.0 Hz, 1H), 4.20 (q, J = 7.1 Hz, 2H), 3.01 (t, J = 6.2 Hz, 2H), 2.33 (t, J = 6.1 Hz, 2H), 1.90-1.84 ( m, 2H), 1.76-1.70 (m, 2H), 1.28 (t, J = 7.1 Hz, 3H).

Preparation of ( E ) -3- (2-Styrylphenyl) -4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazole

[Cp * RhCl ₂ ] ₂ (3.09 mg, 0.005 mmol) and Cu (OAc) ₂ (36.3 mg, 0.2 mmol), 3-phenyl-4,5,6,7-tetrahydrobenzo [ d in DCE solvent (2 mL). ] [1,2] selenazole (52.45 mg, 0.2 mmol) and styrene (0.028 mL, 0.24 mmol) are added and reacted at 90 ^o C for 1 hour. After the reaction is completed, the solvent is removed using an evaporator. The column (Tetrahydrofuran: Haxane = 1: 30) was carried out to obtain the desired compound ( E ) -3- (2-styrylphenyl) -4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazole (65.9 g , 90%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.75 (d, J = 7.9 Hz, 1H), 7.43-7.39 (m, 1H), 7.35-7.27 (m, 6H), 7.24-7.17 (m, 1H), 6.98 ( d, J = 16.3 Hz, 1H), 6.90 (d, J = 16.3 Hz, 1H), 3.00 (t, J = 6.2 Hz, 2H), 2.33 (t, J = 6.2 Hz, 2H), 1.85-1.799 ( m, 2H), 1.71-1.65 (m, 2H).

Preparation of ( E ) -3- (2- (4-Methylstyryl) phenyl) -4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazole

[Cp * RhCl ₂ ] ₂ (3.09 mg, 0.005 mmol) and Cu (OAc) ₂ (36.3 mg, 0.2 mmol), 3-phenyl-4,5,6,7-tetrahydrobenzo [ d in DCE solvent (2 mL). ] [1,2] selenazole (52.45 mg, 0.2 mmol) and 1-methyl-4-vinylbenzene (0.032 mL, 0.24 mmol) are added and reacted at 90 ^o C for 1 hour. After the reaction is completed, the solvent is removed using an evaporator. The column (Tetrahydrofuran: Haxane = 1: 30) was carried out to obtain the desired compound ( E ) -3- (2- (4-methylstyryl) phenyl) -4,5,6,7-tetrahydrobenzo [ d ] [1,2 ] selenazole (62.1 g, 82%) was obtained. ¹ H NMR (400 MHz, CDCl ₃ ) d 7.73 (d, J = 7.9 Hz, 1H), 7.42-7.38 (m, 1H), 7.32-7.22 (m, 4H), 7.10 (d, J = 8.0 Hz, 2H) , 6.95 (d, J = 16.3 Hz, 1H), 6.84 (d, J = 16.3 Hz, 1H), 3.00 (t, J = 6.2 Hz, 2H), 2.34-2.30 (m, 5H), 1.85-1.80 ( m, 2H), 1.71-1.65 (m, 2H).

Preparation of ( E ) -3- (2- (4-Chlorostyryl) phenyl) -4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazole

[Cp * RhCl ₂ ] ₂ (3.09 mg, 0.005 mmol) and Cu (OAc) ₂ (36.3 mg, 0.2 mmol), 3-phenyl-4,5,6,7-tetrahydrobenzo [ d in DCE solvent (2 mL). ] [1,2] selenazole (52.45 mg, 0.2 mmol) and 1-chloro-4-vinylbenzene (0.029 mL, 0.24 mmol) are added and reacted at 90 ^o C for 1 hour. After the reaction is completed, the solvent is removed using an evaporator. Then, the column (Tetrahydrofuran: Haxane = 1: 30) was carried out to obtain the desired compound ( E ) -3- (2- (4-chlorostyryl) phenyl) -4,5,6,7-tetrahydrobenzo [ d ] [1,2 ] selenazole (65.8 g, 83%) was obtained. ¹ H NMR (400 MHz, CDCl ₃ ) d 7.73 (d, J = 7.8 Hz, 1H), 7.43-7.39 (m, 1H), 7.31 (td, J = 11.1 Hz, J = 1.2 Hz, 1H), 7.28 (dd , J = 7.6 Hz, J = 1.5 Hz, 1H), 7.25 (s, 4H), 3.00 (t, J = 6.2 Hz, 2H), 2.33 (t, J = 6.1 Hz, 2H), 1.86-1.80 (m , 2H), 1.71-1.66 (m, 1H).

Preparation of 4-Methyl- N- (2- (4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazol-3-yl) phenyl) benzenesulfonamide

[Cp * IrCl ₂ ] ₂ (6.39 mg, 0.008 mmol) and AgPF ₆ (8.09 mg, 0.032 mmol), 3-phenyl-4,5,6,7-tetrahydrobenzo [ d ] [1 in DCE solvent (1 mL) , 2] selenazole (52.45 mg, 0.2 mmol) and 4-methylbenzenesulfonyl azide (47.3 mg, 0.24 mmol) were added and reacted at 80 ^° C. for 3 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ethyl acetate: DCM: Haxane = 1: 1: 10) was carried out to obtain the desired compound, 4-methyl- N- (2- (4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazol -3-yl) phenyl) benzene-sulfonamide (82.0 mg, 95%) was obtained. ¹ H NMR (400 MHz, CDCl ₃ ) d 9.77 (s, 1H), 7.75 (dd, J = 8.1 Hz, J = 0.9 Hz, 1H), 7.39-7.35 (m, 1H), 7.26-7.14 (m, 4H) , 6.98 (d, J = 8.0 Hz, 2H), 2.93 (t, J = 6.3 Hz, 2H), 2.30 (s, 3H), 2.12 (t, J = 6.1 Hz, 2H), 1.84-1.78 (m, 2H), 1.57-1.51 (m, 2H).

Preparation of 4-Chloro- N- (2- (4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazol-3-yl) phenyl) benzenesulfon-amide

[Cp * IrCl ₂ ] ₂ (6.39 mg, 0.008 mmol) and AgPF ₆ (8.09 mg, 0.032 mmol), 3-phenyl-4,5,6,7-tetrahydrobenzo [ d ] [1 in DCE solvent (1 mL) , 2] selenazole (52.45 mg, 0.2 mmol) and 4-chlorobenzenesulfonyl azide (52.2 mg, 0.24 mmol) were added and reacted at 80 ^° C. for 3 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ethyl acetate: DCM: Haxane = 1: 1: 10) was carried out to obtain the desired compound 4 - chloro- N- (2- (4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazol -3-yl) phenyl) benzene-sulfonamide (89.7 g, 99%) was obtained. ¹ H NMR (400 MHz, CDCl ₃ ) d 9.91 (s, 1H), 7.76-7.74 (m, 1H), 7.43-7.39 (m, 1H), 7.27-7.20 (m, 4H), 7.16-7.13 (m, 2H ), 2.93 (t, J = 6.2 Hz, 2H), 2.17 (t, J = 6.1 Hz, 2H), 1.86-1.80 (m, 2H), 1.66-1.60 (m, 2H).

Preparation of N- (2- (4,5,6,7-Tetrahydrobenzo [ d ] [1,2] selenazol-3-yl) phenyl) methanesulfonamide

[Cp * IrCl ₂ ] ₂ (6.39 mg, 0.008 mmol) and AgPF ₆ (8.09 mg, 0.032 mmol), 3-phenyl-4,5,6,7-tetrahydrobenzo [ d ] [1 in DCE solvent (1 mL) , 2] selenazole (52.45 mg, 0.2 mmol) and methanesulfonyl azide (29.1 mg, 0.24 mmol) were added and reacted at 80 ^° C. for 3 hours. After the reaction is completed, the solvent is removed using an evaporator. Then, the column (Ethyl acetate: DCM: Haxane = 1: 1: 10) was carried out and the desired compound N- (2- (4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazol-3-yl ) phenyl) methanesulfonamide (50.4 g, 71%) was obtained. ¹ H NMR (400 MHz, CDCl ₃ ) d 9.17 (s, 1H), 7.71-7.69 (m, 1H), 7.43-7.39 (m, 2H), 7.23-7.19 (m, 1H), 3.03 (t, J = 6.3 Hz, 2H), 2.63 (t, J = 6.1 Hz, 2H), 1.95-1.89 (m, 2H), 1.79-1.73 (m, 2H) .

Preparation of 3-([1,1'-Biphenyl] -2-yl) -4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazole

[Cp * IrCl ₂ ] ₂ (7.97 mg, 0.01 mmol), AgNTf ₂ (11.6 mg, 0.03 mmol), 3-phenyl-4,5,6,7-tetrahydrobenzo [ d ] [1 in DCE solvent (1 mL) , 2] selenazole (62.9 mg, 0.24 mmol) and diphenyliodonium trifluoromethanesulfonate (86.04 mg, 0.2 mmol) were added and then reacted at 75 ^° C. for 3 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Tetrahydrofuran: Haxane = 1: 100) was carried out to obtain the desired compound 3-([1,1'-biphenyl] -2-yl) -4,5,6,7-tetrahydrobenzo [ d ] [1,2 ] selenazole (38.3 mg, 57%) was obtained. ¹ H NMR (400 MHz, CDCl ₃ ) d 7.49-7.46 (m, 2H), 7.43-7.38 (m, 2H), 7.25-7.19 (m, 3H), 7.18-7.16 (m, 2H), 2.88 (t, J = 6.3 Hz, 2H), 1.85 (s, 2H), 1.61-1.58 (m, 2H), 1.44-1.38 (m, 2H).

Preparation of 3- (4'-Methyl- [1,1'-biphenyl] -2-yl) -4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazole

[Cp * IrCl ₂ ] ₂ (7.97 mg, 0.01 mmol), AgNTf ₂ (11.6 mg, 0.03 mmol), 3-phenyl-4,5,6,7-tetrahydrobenzo [ d ] [1 in DCE solvent (1 mL) , 2] selenazole (62.9 mg, 0.24 mmol) and di- p- tolyliodonium trifluoromethanesulfonate (86.04 mg, 0.2 mmol) were added and then reacted at 75 ^° C. for 3 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Tetrahydrofuran: Haxane = 1: 100) was carried out to obtain the desired compound 3- (4'-methyl- [1,1'-biphenyl] -2-yl) -4,5,6,7-tetrahydrobenzo- [ d ] [1,2] selenazole (50.1 g, 71%) was obtained. ¹ H NMR (400 MHz, CDCl ₃ ) d 7.47-7.44 (m, 2H), 7.41-7.36 (m, 2H), 7.07-7.02 (m, 4H), 2.84 (t, J = 6.2 Hz, 2H), 2.31 ( s, 3H), 1.61-1.57 (m, 2H), 1.46-1.40 (m, 2H).

Preparation of 3- (4'-Chloro- [1,1'-biphenyl] -2-yl) -4,5,6,7-tetrahydrobenzo [ d ] [1,2] selenazole

[Cp * IrCl ₂ ] ₂ (7.97 mg, 0.01 mmol), AgNTf ₂ (11.6 mg, 0.03 mmol), 3-phenyl-4,5,6,7-tetrahydrobenzo [ d ] [1 in DCE solvent (1 mL) , 2] selenazole (62.9 mg, 0.24 mmol) and bis (4-chlorophenyl) iodonium trifluoromethanesulfonate (99.81 mg, 0.2 mmol) were added and then reacted at 75 ^° C. for 3 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Tetrahydrofuran: Haxane = 1: 100) was carried out to the desired compound 3- (4'-chloro- [1,1'-biphenyl] -2-yl) -4,5,6,7-tetrahydrobenzo- [ d ] [1,2] selenazole (36.5 g, 49%). ¹ H NMR (400 MHz, CDCl ₃ ) d 7.50-7.45 (m, 1H), 7.43-7.39 (m, 3H), 7.22-7.19 (m, 2H), 7.12-7.09 (m, 2H), 2.85 (t, J = 6.3 Hz, 2H), 1.88-1.87 (m, 2H), 1.67-1.61 (m, 2H), 1.49-1.43 (m, 2H).

Claims (9)

delete delete A selenium ring compound synthesis method, which proceeds according to a reaction formula represented by the following formula (5).

'

(5)

In Formula 5, R ¹ and R ² are each a hydrogen, a halogen group, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, or a substituted or unsubstituted carbon group having 6 to 12 carbon atoms. Unsubstituted aryl group, substituted or unsubstituted heteroaryl group having 5 to 12 carbon atoms and alkyloxy group having 1 to 10 carbon atoms, and R ¹ and R ² may be connected to each other to form a fused ring. And
R ⁴ is hydrogen, a halogen group, an alkyl group of 1 to 10 carbon atoms, an alkenyl group of 2 to 10 carbon atoms, an alkynyl group of 2 to 10 carbon atoms, a substituted or unsubstituted aryl group of 6 to 12 carbon atoms, a substituted or unsubstituted carbon A heteroaryl group of 5 to 12, a haloalkyl group of 1 to 10 carbon atoms, an alkoxy group of 1 to 10 carbon atoms, or an alkylphenyl group of 7 to 15 carbon atoms, and M is a metal catalyst including rhodium) delete delete delete As a novel selenium ring compound,
A novel selenium ring compound synthesized by the method according to claim 3 and having the structure of any one of the following structures.

delete delete