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Method for synthesizing sulfone compounds under photocatalysis condition

A photocatalytic and compound technology, applied in the preparation of organic compounds, chemical instruments and methods, organic compound/hydride/coordination complex catalysts, etc., can solve the problems of limited universality of substrates and harsh reaction conditions , to achieve the effect of broadening new applications, low prices, and wide sources

Active Publication Date: 2021-03-30
HENAN UNIVERSITY
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0006] In summary, in the current reports on the direct synthesis of sulfone compounds from simple and easy-to-obtain substrates, there are still problems such as harsh reaction conditions and limited universality of substrates.
With polyacid salts as photosensitizers, the current stage mainly focuses on the construction of C-C bonds, but there is no report on the construction of C-S bonds.

Method used

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  • Method for synthesizing sulfone compounds under photocatalysis condition
  • Method for synthesizing sulfone compounds under photocatalysis condition
  • Method for synthesizing sulfone compounds under photocatalysis condition

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Experimental program
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Embodiment 1

[0039] The preparation of embodiment 1 diphenylsulfone

[0040] Get a quartz reaction tube, add a magnetic stirrer thereto, then add 0.3mmol of phenylhydrazine, 0.9mmol of sodium benzenesulfinate, 0.9mmol of cesium carbonate (Cs2 CO 3 ), 5mmol% photosensitizer polyacid salt ([(n-Bu 4 )N] 4 [W 10 o 32 ], TBADT), and finally 1 mL of dimethyl sulfoxide (DMSO) was added.

[0041] Then add a three-way gas guide head with a balloon above the quartz reaction tube, first use liquid nitrogen to freeze the reaction stock solution completely, then use an oil pump to evacuate the quartz reaction tube, and then fill the balloon with oxygen; stir with a magnetic stirrer Under the condition of oxygen, the reaction was carried out under the irradiation of blue LED light for 12 hours, the final product was detected by TLC, and finally the final product diphenyl sulfoxide was obtained by separation by column chromatography with a yield of 58%.

[0042] The reaction equation is as follows: ...

Embodiment 2

[0046] The preparation of embodiment 2 4-methyldiphenyl sulfone

[0047] Get a quartz reaction tube, add a magnetic stirrer thereto, then add 0.3mmol of 4-methylphenylhydrazine, 0.9mmol of sodium benzenesulfinate, 0.9mmol of cesium carbonate (Cs 2 CO 3 ), 5 mmol% photosensitizer Eosin Y, and finally 1 mL of dimethyl sulfoxide (DMSO) was added.

[0048] Then add a three-way gas guide head with a balloon above the quartz reaction tube, first use liquid nitrogen to freeze the reaction stock solution completely, then use an oil pump to evacuate the quartz reaction tube, and then fill the balloon with oxygen; stir with a magnetic stirrer Under the condition of oxygen, the reaction was carried out under the irradiation of blue LED light for 12 h, the final product was detected by TLC, and finally the final product 4-methyldiphenyl sulfone was obtained by separation by column chromatography with a yield of 52%.

[0049] The reaction equation is as follows:

[0050]

[0051] 4-M...

Embodiment 3

[0052] The preparation of embodiment 3 4-cyanodiphenyl sulfone

[0053] Get a quartz reaction tube, add a magnetic stirrer thereto, then add 0.3mmol of 4-cyanophenylhydrazine, 0.9mmol of sodium benzenesulfinate, 0.9mmol of cesium carbonate (Cs 2 CO 3 ), 15mmol% photosensitizer polyacid salt ([(n-Bu 4 )N] 4 [W 10 o 32 ], TBADT), and finally 1 mL of dimethyl sulfoxide (DMSO) was added.

[0054] Then add a three-way gas guide head with a balloon above the quartz reaction tube, first use liquid nitrogen to freeze the reaction stock solution completely, then use an oil pump to evacuate the quartz reaction tube, and then fill the balloon with oxygen; stir with a magnetic stirrer Under the condition of oxygen, the reaction was carried out under the irradiation of blue LED light for 12 h, the final product was detected by TLC, and finally the final product 4-cyanodiphenyl sulfone was obtained by separation by column chromatography with a yield of 87%.

[0055] The reaction equat...

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Abstract

The invention belongs to the technical field of compound preparation, and particularly relates to a method for synthesizing sulfone compounds under a photocatalysis condition. Aromatic hydrazine and sulfinate are used as raw materials, and under the action of alkali and a solvent, a sulfone compound is generated through reaction under the condition of air or oxygen under the illumination of visible light. According to the method disclosed by the invention, aryl hydrazine is used as an arylation reagent, polyacid salt is used as a catalyst or an organic photosensitizer is used as a catalyst, and the sulfones compound can be efficiently synthesized by coupling with sulfinate under the condition of room temperature through visible light irradiation. The method has good substrate universalityand relatively mild reaction conditions, is not only a substitute for synthesizing sulfone compounds by coupling from simple substrates reported at present, but also broadens the new application of the polyacid salt in the field of photocatalysis.

Description

technical field [0001] The invention belongs to the technical field of compound preparation, and in particular relates to a method for synthesizing sulfone compounds under photocatalytic conditions. Background technique [0002] As an important class of organic synthesis intermediates, sulfone compounds are widely used in the synthesis of chemistry, medicine, pesticides and materials science. In the synthesis of sulfone compounds from simple substrates, the coupling of halogenated aromatic hydrocarbons and phenylboronic acid as arylation reagents to sulfinates is one of the most commonly used synthetic strategies. [0003] The case where a halogenated aromatic hydrocarbon is used as an arylation agent is as follows. In 1995, Suzuki et al. reported for the first time that aryl halides and sodium sulfinate were catalyzed by CuI to obtain sulfone compounds (Tetrahedron. Lett., 1995, 36, 6239-6242). In the following period of time, the strategy of using halogenated aromatic hy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C315/00C07C317/14C07C317/44C07C317/22C07C317/24C07D213/71C07D277/76B01J31/18B01J31/02
CPCC07C315/00C07D213/71C07D277/76B01J27/188B01J27/19B01J31/0241B01J31/0242B01J31/0244B01J31/0271B01J31/0231B01J31/0235C07C2601/02C07C2601/14B01J35/39C07C317/14C07C317/44C07C317/22C07C317/24
Inventor 徐浩吴存落刘保英李建通张文凯任艳蓉王延鹏丁涛徐元清房晓敏
Owner HENAN UNIVERSITY
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