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A kind of preparation method of aromatic sulfide 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 effects of high reaction efficiency, low cost and good catalytic activity

Active Publication Date: 2021-06-25
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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  • A kind of preparation method of aromatic sulfide compound
  • A kind of preparation method of aromatic sulfide compound
  • A kind of preparation method of aromatic sulfide 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 sulfide compound, belonging to the technical field of catalysis. The invention provides a new green and environment-friendly method to efficiently synthesize thioether derivatives. Under the action of a catalyst, thiophenols and aryl diazonium salt compounds are directly coupled under light to generate aromatic thioether compounds; wherein the catalyst is Cercosporium Bacteria. The method of the invention uses cercosporin as a catalyst, the catalytic conditions are relatively mild, and it can be carried out at room temperature and under the irradiation of visible light. The catalytic activity of the catalyst is high, and it can catalyze the synthesis of thioether compounds with high selectivity. A small amount of catalyst can make the yield increase. Reach above 96%. The photocatalyst and the substrate raw materials of the invention are simple and easy to obtain, are environmentally friendly, low in cost, can be mass-produced, and have very good application prospects.

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 Patents(China)
IPC IPC(8): C07C319/14B01J31/02C07C323/20C07C323/09C07C321/30
CPCB01J31/0208B01J35/004B01J2231/4205C07C319/14C07C323/20C07C323/09C07C321/30
Inventor 刘昌梅饶义剑李佳张艳包文豪
Owner JIANGNAN UNIV
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