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Preparation method of aromatic thioether compound

A technology of aromatic sulfides and compounds, applied in the field of catalysis, can solve the problems of pollution and high cost, and achieve the effect of high reaction efficiency, low cost and good application prospect of the process

Active Publication Date: 2019-12-13
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The existing catalysts for the preparation of aryl sulfide compounds are metal catalysts, which have the problems of high cost and easy pollution

Method used

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  • Preparation method of aromatic thioether compound
  • Preparation method of aromatic thioether compound
  • Preparation method of aromatic thioether compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Embodiment 1. Catalyzed synthesis of 4-methoxy-4'-methyl-diphenylsulfide by cercosporin catalyst

[0046] Add cercosporin (0.005mmol), p-methoxybenzenetetrafluoroborate diazonium salt (0.6mmol), p-methylthiophenol (0.5mmol), 2mL DMSO in a 10mL reaction tube in turn, and then , 15W white light irradiation, room temperature 25 ℃ reaction 20h. The reaction solution was washed three times with water, and the organic phase was collected and then dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated to dryness by rotary evaporation, and the thin-layer silica gel plate of 300-500 mesh was used for rapid separation, and the eluent used was ethyl acetate / petroleum ether (v:v=3:100) to obtain 4-methoxy-4' -Methyl-diphenyl sulfide, the productive rate is 87%, the product 1 H-NMR spectrum see figure 1 .

Embodiment 2

[0047] Embodiment 2. Catalyzed synthesis of 4-chloro-4'-methyl-diphenyl sulfide by cercosporin catalyst

[0048] Add cercosporin (0.005mmol), p-chlorobenzenetetrafluoroborate diazonium salt (0.6mmol), p-methylthiophenol (0.5mmol), 2mL DMSO in a 10mL reaction tube in turn, and then in air, 15W White light irradiation, room temperature 25 ℃ reaction 20h. The reaction solution was washed three times with water, and the organic phase was collected and then dried over anhydrous magnesium sulfate. Filtrate, dry the solvent by rotary evaporation, and then use a 300-500 mesh thin-layer silica gel plate for rapid separation. The eluent used is ethyl acetate / petroleum ether (v:v=3:100) to obtain 4-chloro-4'-formazan Base-diphenyl sulfide, the productive rate is 65%, the product 1 H-NMR spectrum see figure 2 .

Embodiment 3

[0049] Embodiment 3. Catalyzed synthesis of 4-nitro-4'-methyl-diphenyl sulfide by cercosporin catalyst

[0050]Add cercosporin (0.005mmol), p-nitrobenzenetetrafluoroborate diazonium salt (0.6mmol), p-methylthiophenol (0.5mmol), 2mL DMSO successively into a 10mL reaction tube, and then in air, 15W white light irradiation, room temperature 25 ℃ reaction 20h. The reaction solution was washed three times with water, and the organic phase was collected and then dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated to dryness by rotary evaporation, and then separated quickly with a 300-500 mesh thin-layer silica gel plate, and the eluent used was ethyl acetate / petroleum ether (v:v=3:100) to obtain 4-nitro-4'- Methyl-diphenyl sulfide, productive rate is 80%, the product 1 H-NMR spectrum see image 3 .

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Abstract

The invention discloses a preparation method of an aromatic thioether compound, belonging to the technical field of catalysis. The invention provides a novel environment-friendly method for efficiently synthesizing a thioether derivative; and under the action of a catalyst, thiophenol and an aryl diazonium salt compound are directly coupled under illumination to generate the aromatic thioether compound, wherein the catalyst is cephalosporin. According to the method disclosed by the invention, the cephalosporin is used as the catalyst; catalytic conditions are mild, and the method can be carried out at room temperature under visible light irradiation; the catalytic activity of the catalyst is high, and the thioether compound can be catalytically synthesized with high selectivity; and the yield of the thioether compound can reach 96% or above by virtue of a trace amount of the catalyst. The photocatalyst disclosed by the invention has the advantages of usage of simple and easily available substrate raw materials, environmental friendliness, low cost and very good application prospect, and can be produced on a large scale.

Description

technical field [0001] The invention belongs to the technical field of catalysis, and in particular relates to a preparation method of an aromatic sulfide compound. Background technique [0002] Photocatalysis has attracted considerable attention for using abundant, cheap, and renewable light sources to drive chemical reactions. In most photocatalytic processes, highly reactive radical ions are generated by photoinduced electron transfer (PET). Among them, pyridine complexes of ruthenium and iridium are the most widely used transition metal photocatalysts. However, metal photocatalysts have the disadvantages of high cost and easy environmental pollution, which limit their applications. Therefore, it is of great significance to develop green and economical metal-free photocatalysts. [0003] Cercosporin has attracted extensive attention due to its strong visible light absorption and excellent properties of being able to generate reactive oxygen species. Although cercospor...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C319/14B01J31/02C07C323/20C07C323/09C07C321/30
CPCC07C319/14B01J31/0208B01J2231/4205B01J35/39C07C323/20C07C323/09C07C321/30
Inventor 刘昌梅饶义剑李佳张艳包文豪
Owner JIANGNAN UNIV
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