CN112409232B - Method for synthesizing asymmetric aryl selenide and aryl tellurium ether based on aryl azo sulfone - Google Patents

Method for synthesizing asymmetric aryl selenide and aryl tellurium ether based on aryl azo sulfone Download PDF

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CN112409232B
CN112409232B CN202011143135.5A CN202011143135A CN112409232B CN 112409232 B CN112409232 B CN 112409232B CN 202011143135 A CN202011143135 A CN 202011143135A CN 112409232 B CN112409232 B CN 112409232B
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CN112409232A (en
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芦逵
刘俊杰
赵霞
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Tianjin University of Science and Technology
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C391/00—Compounds containing selenium
    • C07C391/02—Compounds containing selenium having selenium atoms bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C395/00—Compounds containing tellurium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/61—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

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Abstract

The invention belongs to the field of new preparation methods of new compounds, and particularly relates to a method for synthesizing asymmetric aryl selenides and tellurides by carrying out cross-coupling reaction on aryl azosulfone and diselenide or ditelluride under the irradiation of visible light. The structural general formula of the compound is shown as the following figure, wherein R 1 Is halogen, ester group, methyl or methoxy; r 2 Is an aryl group; the method is applied to synthesize a series of asymmetric aryl selenides and tellurides for the first time, and has wide prospects in the aspect of establishing synthesis application of the compound library.

Description

Method for synthesizing asymmetric aryl selenide and aryl tellurium ether based on aryl azo sulfone
Technical Field
The invention relates to the field of organic synthesis, in particular to an organic synthesis method for synthesizing asymmetric aryl selenide and aryl telluride by cross-coupling reaction of aryl azo sulfone derivatives and diselenide or ditelluride.
Technical Field
Asymmetric aryl selenides and aryl tellurides are important organic structural units, are widely applied to agriculture, pharmacy and material science, have various biological activities such as oxidation resistance, tumor resistance and the like, and are concerned by organic chemists of various countries in synthesis.
The current methods for synthesizing arylselenides and tellurides are mainly to obtain asymmetric arylselenides and tellurides by reacting a series of aromatic substrates such as aryl halides, arylboronic acids and the like with diselenide or ditelluride. The above process either requires the use of noble metal silver salts as catalysts or the use of air-sensitive and expensive photosensitizers. This leaves a wide space for the subsequent development of new methods for synthesizing such compounds.
Disclosure of Invention
The purpose of the invention is:
under the induction of visible light, aryl azo sulfone derivatives are directly reacted with diselenide or ditelluroether to synthesize asymmetric aryl selenides and tellurides.
The purpose of the invention is realized by the following technical scheme:
Figure GSB0000201325780000011
the nomenclature and structures of the synthesized symmetric arylselenides and tellurides are shown in the following table:
TABLE 1 nomenclature and Structure of asymmetric arylselenides and tellurides
Figure GSB0000201325780000021
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Figure GSB0000201325780000031
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Figure GSB0000201325780000041
The invention has the advantages and positive effects that:
1. the raw materials are cheap and easy to obtain.
2. No metal catalyst and photosensitizer need be used.
3. The method is simultaneously suitable for preparing the aryl selenide and the aryl telluride.
Detailed Description
For understanding the present invention, the present invention will be further described with reference to the following examples: the following examples are illustrative and not intended to be limiting, and are not intended to limit the scope of the invention.
The structural formulas of the asymmetric aryl selenide and the aryl telluride are shown as the following figures:
Figure GSB0000201325780000042
the specific nomenclature and structure are shown in table 1 above.
The above asymmetric aryl selenides and aryl tellurides are synthesized by the following general synthesis method:
adding aryl azo sulfone derivative (0.3 mmol), diselenide or ditelluride (0.36 mmol) and acetonitrile (3 mL) into a 10mL branch pipe in sequence, reacting under the irradiation of a 21W blue LED lamp, detecting the reaction by a dot plate after 21-24h, taking petroleum ether and ethyl acetate = 15: 1-30: 1 as a mobile phase, and carrying out column chromatography to obtain the compounds shown in the table 1, wherein the yield is 38-91%.
The following examples are given to illustrate the present invention.
Example 1
(the structure is shown in the following figure).
Figure GSB0000201325780000043
The synthesis method of example 1 is the same as the general synthesis method described above.
Yellow oil; yield: 91 percent.
1 H NMR(400MHz，CDCl 3 )：δ7.88(d，J＝8.4Hz，2H)，7.58-7.56(m，2H)，7.39-7.32(m，5H)，4.35(q，J＝7.2Hz，2H)，1.37(t，J＝7.2Hz，3H). 13 C NMR(100MHz，CDCl 3 )：δ166.3，139.3，134.8，130.5，130.1，129.6，128.9，128.7，128.4，60.9，14.3.
Example 2
(the structure is shown in the following figure).
Figure GSB0000201325780000051
The synthesis method of example 2 is the same as the general synthesis method described above.
Yellow oil; yield: 78 percent.
1 H NMR(400MHz，CDCl 3 )：δ7.60-7.58(m，2H)，7.35-7.32(m，3H)，7.21-7.16(m，1H)，6.95(dd，J＝7.8，1.6Hz，1H)，6.85(d，J＝8.2Hz，1H)，6.81-6.77(m，1H)，3.88(s，3H). 13 C NMR(100MHz，CDCl 3 )：δ156.5，135.4，130.7，129.4，128.2，128.1，127.6，121.8，121.6，110.3，55.8.
Example 3
(the structure is shown in the following figure).
Figure GSB0000201325780000052
The synthesis method of example 3 is the same as the general synthesis method described above.
Yellow oil; yield: 91 percent.
1 H NMR(400MHz，CDCl 3 )：δ7.53-7.49(m，3H)，7.34-7.29(m，4H)，7.22(d，J＝8.4Hz，1H). 13 C NMR(100MHz，CDCl 3 )：δ133.9，133.3，133.1，131.5，131.3，131.2，130.8，129.6，129.4，128.2.
Example 4
(the structure is shown in the following figure).
Figure GSB0000201325780000053
The synthesis method of example 4 is the same as the above synthesis method.
A white solid; yield: 56 percent.
1 H NMR(400MHz，CDCl 3 )：δ7.43(d，J＝7.6Hz，2H)，7.27-7.26(m，3H)，6.45(s，2H)，3.84(s，3H)，3.79(s，6H). 13 C NMR(100MHz，CDCl 3 )：δ153.5，137.8，135.5，131.9，129.2，127.0，124.3，111.0，60.8，56.1.HRMS(ESI)m/z calcd for C 15 H 17 O 3 Se[M+H] + 325.0337；found 325.0340.
Example 5
(the structure is shown in the following figure).
Figure GSB0000201325780000061
The synthesis method of example 5 is the same as the general synthesis method described above.
A yellow solid; yield: and 55 percent.
1 H NMR(400MHz，CDCl 3 )：δ7.99(s，1H)，7.81-7.89(m，1H)，7.73(d，J＝8.0Hz，2H)，7.50-7.46(m，4H)7.28-7.27(m，3H). 13 C NMR(100MHz，CDCl 3 )：δ134.0，132.9，132.4，132.0，131.2，130.4，129.3，128.8，128.4，127.7，127.4，127.3，126.5，126.2.
Example 6
(the structure is shown in the following figure).
Figure GSB0000201325780000062
The synthesis method of example 6 is the same as the general synthesis method described above.
Yellow oil; yield: 86 percent.
1 H NMR(400MHz，CDCl 3 )：δ7.92(d，J＝8.0Hz，2H)，7.68(t，J＝1.8Hz，1H)，7.47-7.41(m，4H)，7.19(t，J＝8.0Hz，1H)，4.36(q，J＝7.2Hz，2H)，1.38(t，J＝7.2Hz，3H). 13 C NMR(100MHz，CDCl 3 )：δ166.0，137.7，136.4，132.5，131.3，131.2，130.8，130.3，129.2，123.2，61.0，14.3.HRMS(ESI)m/z calcd for C 15 H 14 BrO 2 Se[M+H] + 384.9337；found 384.9340.
Example 7
(the structure is shown in the following figure).
Figure GSB0000201325780000063
The synthesis method of example 7 is the same as the general synthesis method described above.
Yellow oil; yield: 82 percent.
1 H NMR(400MHz，CDCl 3 )：δ7.53(d，J＝8.0Hz，2H)，7.41(t，J＝1.8Hz，1H)，7.29(d，J＝8.0Hz，1H)，7.20(d，J＝8.0Hz，1H)，7.07(t，J＝8.0Hz，1H)，6.89(d，J＝8.0Hz，2H)，3.83(s，3H). 13 C NMR(100MHz，CDCl 3 )：δ160.1，137.1，135.7，132.6，130.2，129.2，128.7，123.1，118.7，115.3，55.2.
Example 8
(the structure is shown in the following figure).
Figure GSB0000201325780000071
The synthesis method of example 8 is the same as the general synthesis method described above.
Yellow oil; yield: 38 percent.
1 H NMR(400MHz，CDCl 3 )：δ7.98-7.84(m，2H)，7.58-7.49(m，6H)，4.37(q，J＝6.8Hz，2H)，1.39(t，J＝6.8Hz，3H). 19 F NMR(376MHz，CDCl 3 )：δ-62.73，(s，3F). 13 C NMR(100MHz，CDCl 3 )：δ166.0，136.5，135.4，133.0，132.5，130.5，130.2(q，J＝15.3Hz，1C)，129.8，126.2(q，J＝3.7Hz，1C)，123.9(q，J＝271.3Hz，1C)，61.1，14.3.
Example 9
(the structure is shown in the following figure).
Figure GSB0000201325780000072
The synthesis of example 9 was performed as described above.
Yellow oil; yield: 70 percent.
1 H NMR(400MHz，CDCl 3 )：δ7.88(d，J＝8.4Hz，2H)，7.39(d，J＝8.4Hz，2H)，7.24(t，J＝7.8Hz，1H)，7.14-7.12(m，1H)，7.11-7.10(m，1H)，6.90-6.87(m，1H)，4.35(q，J＝7.2Hz，2H)，3.77(s，3H)，1.37(t，J＝7.2Hz，3H). 13 C NMR(100MHz，CDCl 3 )：δ166.2，139.1，130.6，130.1，129.7，128.6，126.8，119.7，114.3，60.9，55.3，14.2.HRMS(ESI)m/z calcdfor C 16 H 17 O 3 Se[M+H] + 337.0337；found 337.0333.
Example 10
(the structure is shown in the following figure).
Figure GSB0000201325780000081
The synthesis method of example 10 is the same as the general synthesis method described above.
Yellow oil; yield: 53 percent.
1 H NMR(400MHz，CDCl 3 )：δ7.48(d，J＝8.8Hz，2H)，7.18(d，J＝7.2Hz，1H)，7.14-7.08(m，2H)，7.04-7.00(m，1H)，6.88(d，J＝8.8Hz，2H)，3.83(s，3H)，2.40(s，3H). 13 C NMR(100MHz，CDCl 3 )：δ159.7，137.8，136.6，133.9，130.7，130.0，126.5，126.5，119.2，115.2，55.2，21.8.
Example 11
(the structure is shown in the following figure).
Figure GSB0000201325780000082
The synthesis method of example 12 is the same as the general synthesis method described above.
A yellow solid; yield: 87 percent.
1 H NMR 400MHz，CDCl 3 )：δ7.77(d，J＝2.0Hz，1H)，7.59-7.56(m，2H)，7.44-7.42(m，1H)，7.41-7.35(m，4H). 13 C NMR(100MHz，CDCl 3 )：δ148.1，135.2，134.9，133.2，132.1，130.0，129.1，127.9，127.2，124.9.HRMS(ESI)m/z calcd for C 12 H 9 ClNO 2 Se[M+H] + 313.9482；found 313.9487.
Example 12
(the structure is shown in the following figure).
Figure GSB0000201325780000083
The synthesis method of example 13 is the same as the general synthesis method described above.
Yellow oil; yield: and 75 percent.
1 H NMR(400MHz，CDCl 3 )：δ7.88(d，J＝8.5Hz，2H)，7.59-7.56(m，2H)，7.39-7.32(m，5H)，4.35(q，J＝7.2Hz，2H)，1.37(t，J＝7.2Hz，3H). 13 C NMR(100MHz，CDCl 3 )：δ166.2，139.4，134.8，130.4，130.1，129.6，128.8，128.6，128.4，60.9，14.3.
Example 13
(the structure is shown in the following figure).
Figure GSB0000201325780000091
The synthesis method of example 14 is the same as the above synthesis method.
Yellow oil; yield: 57 percent.
1 H NMR(400MHz，CDCl 3 )：δ7.60-7.57(m，2H)，7.48-7.43(m，4H)，7.39-7.33(m，3H)， 19 F NMR(376MHz，CDCl 3 )：δ-62.78，(s，3F). 13 C NMR(100MHz，CDCl 3 )：δ164.0，152.3，145.1，132.0，130.2，(d，J＝191.7Hz，1C)，130.3(q，J＝235.8Hz，1C)，126.9，117.8，112.1，53.5(q，J＝5.1Hz，1C).
Example 14
(the structure is shown in the following figure).
Figure GSB0000201325780000092
The synthesis of example 15 was performed as described above.
Yellow oil; yield: and 47 percent.
1 H NMR(400MHz，CDCl 3 )：δ7.74(d，J＝7.4Hz，2H)，7.58-7.56(m，2H)，7.24-7.16(m，3H)，6.80(d，J＝8.8Hz，2H)，3，81(s，3H). 13 C NMR(100MHz，CDCl 3 )：δ160.0，141.2，136.4，129.3，127.2，115.9，115.5，103.2，55.2.
Example 15
(the structure is shown in the following figure).
Figure GSB0000201325780000093
The synthesis method of example 16 is the same as the general synthesis method described above.
Yellow oil; yield: and 48 percent.
1 H NMR(400MHz，CDCl 3 )：δ8.92(d，J＝2.0Hz，1H)，8.25(d，J＝2.0Hz，1H)，8.08(d，J＝8.8Hz，1H)，7.72-7.68(m，2H)，7.56-7.54(m，1H)，7.53-7.49(m，2H)，7.32-7.28(m，3H). 13 C NMR(100MHz，CDCl 3 )：δ148.9，142.5，141.7，134.3，131.9，130.1，129.1，128.9，128.9，127.9，127.4，126.7，125.8.HRMS(ESI)m/z calcd for C 15 H 12 NTe[M+H] + 336.0026；found 336.0030.
Example 16
(the structure is shown in the following figure).
Figure GSB0000201325780000101
The synthesis method of example 17 is the same as the synthesis method described above.
Yellow oil; yield: 77 percent.
1 H NMR(400MHz，CDCl 3 )：δ8.36(d，J＝2.2Hz，1H)，7.72(dd，J＝8.4，2.2Hz，1H)，7.35-7.33(m，2H)，7.25-7.19(m，3H)，6.70(d，J＝8.4Hz，1H)，3.93(s，3H). 13 C NMR(100MHz，CDCl 3 )：δ164.0，152.2，145.2，132.0，131.2，129.3，126.9，117.9，112.3，53.7.
Example 17
(the structure is shown in the following figure).
Figure GSB0000201325780000102
The synthesis of example 18 was performed as described above.
Yellow oil; yield: and 78 percent.
1 H NMR(400MHz，CDCl 3 )：δ8.41(d，J＝2.4Hz，1H)，7.65(dd，J＝6.8，2.4Hz，1H)，7.50-7.47(m，2H)，7.33-7.28(m，3H)，7.20(dd，J＝8.2，0.4Hz，1H). 13 C NMR(100MHz，CDCl 3 )：δ152.2，150.3，142.5，133.6，129.7，129.0128.2，127.6，124.9.HRMS(ESI)m/z calcd for C 11 H 8 ClNTeNa[M+Na] + 341.9300；found 341.9301.
Example 18
(the structure is shown in the following figure).
Figure GSB0000201325780000103
The synthesis method of example 19 is the same as the general synthesis method described above.
A yellow solid; yield: and 47 percent.
1 H NMR(400MHz，CDCl 3 )：δ8.89(s，1H)，8.64(d，J＝1.8Hz，1H)，8.56(dd，J＝1.2，4.8Hz，1H)，8.01(dt，J＝7.8，1.8Hz，1H)7.92(dd，J＝2.2，7.2Hz，1H)7.22-7.19(m，2H). 13 C NMR(100MHz，CDCl 3 )：δ157.4，157.3，151.9，149.3，147.4，145.7，125.7，125.0，111.1，109.2.HRMS(ESI)m/z calcd for C 10 H 8 ClN 2 Te[M+H] + 320.9433；found 320.9435.
Example 19
(the structure is shown in the following figure).
Figure GSB0000201325780000111
The synthesis method of example 20 is the same as the general synthesis method described above.
Yellow oil; yield: 53 percent.
1 H NMR(400MHz，CDCl 3 )：δ7.74-7.72(m，2H)，7.46-7.37(m，3H)，7.30(d，J＝5.2Hz，1H)，6.35(d，J＝5.2Hz，1H)，3.92(s，3H). 13 C NMR(100MHz，CDCl 3 )：δ163.0，140.5，136.8，131.0，129.6，129.3，129.2，128.3，122.4，52.1.HRMS(ESI)m/z calcd for C 12 H 10 O 2 STeNa[M+Na] + 370.9356；found 370.9356.

Claims (2)

1. A method for synthesizing asymmetric aryl selenide from aryl azo sulfone and diselenide under photocatalysis is characterized in that under 21W blue light catalysis, aryl azo sulfone and diselenide are used as substrates to synthesize asymmetric aryl selenide, and the specific reaction is as follows, wherein R is 1 Is halogen, methyl or methoxy; r is 2 Is aryl radical
Figure FSB0000201149180000011
2. A method for synthesizing asymmetric aryl telluride from aryl azo sulfone and ditelluroether under photocatalysis is characterized in that under 21W blue light catalysis, the aryl azo sulfone and ditelluroether are used as substrates to synthesize the asymmetric aryl telluride, and the specific reaction is as follows, wherein R is 1 Is halogen, methyl or methoxy; r 2 Is aryl radical
Figure FSB0000201149180000012
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CN107188840A (en) * 2017-05-16 2017-09-22 温州医科大学 A kind of synthetic method of asymmetric diaryl selenide compound

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