Method for photocatalytic synthesis of sulfur sulfone compounds

A technology of thioether compounds and compounds, which is applied in the field of catalysis, can solve the problems of difficult preparation of catalysts, harsh oxidation conditions, and poor reaction selectivity, and achieve the effects of low cost, high reaction efficiency, and mild conditions

Active Publication Date: 2019-05-03
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Most of the reported thioether oxidation systems have defects such as harsh oxidation conditions, poor reaction selectivity, and difficult preparation of catalysts.
In particular, the extensive use of transition metal catalysts such as platinum, copper, and gold has brought serious environmental problems.

Method used

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  • Method for photocatalytic synthesis of sulfur sulfone compounds
  • Method for photocatalytic synthesis of sulfur sulfone compounds
  • Method for photocatalytic synthesis of sulfur sulfone compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Embodiment 1 cercosporin catalyst catalyzes the synthesis of benzyl phenyl sulfone

[0031] Cercosporin (0.005 mmol), benzyl phenyl sulfide (0.5 mmol), and 2 mL of methanol were sequentially added into a 10 mL reaction tube, then protected by oxygen, irradiated with 15W white light, and reacted at room temperature 25 degrees Celsius for 24 hours. The reaction solution was evaporated to dryness by rotary evaporation, and then quickly separated on a 300-500 mesh thin-layer silica gel plate. The eluent used was ethyl acetate / petroleum ether (v:v=1:5) to obtain benzylphenyl sulfone, The yield was 90%.

Embodiment 2

[0032] Embodiment 2 cercosporin catalyst catalyzes the synthesis of benzyl benzyl sulfone

[0033] Cercosporin (0.005 mmol), benzyl benzyl sulfide (0.5 mmol), and 2 mL of methanol were sequentially added into a 10 mL reaction tube, then protected by oxygen, irradiated with 15W white light, and reacted at room temperature 25 degrees Celsius for 24 hours. The reaction solution was evaporated to dryness by rotary evaporation, and then quickly separated with a 300-500 mesh thin-layer silica gel plate. The eluent used was ethyl acetate / petroleum ether (v:v=1:5) to obtain benzylbenzylsulfone, The yield was 95%.

Embodiment 3

[0034] Embodiment 3 cercosporin catalyst catalyzes the synthesis of phenylmethyl sulfone

[0035] Add cercosporin (0.005mmol), phenylmethyl sulfide (0.5mmol) and 2mL methanol successively into a 10mL reaction tube, then protect with oxygen, irradiate with 15W white light, and react at room temperature 25°C for 24h. The reaction solution was evaporated to dryness by rotary evaporation, and then quickly separated on a 300-500 mesh thin-layer silica gel plate. The eluent used was ethyl acetate / petroleum ether (v:v=1:5) to obtain phenylmethyl sulfone, The yield was 90%.

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Abstract

The invention discloses a method for photocatalytic synthesis of sulfur sulfone compounds, and belongs to the technical field of catalysis. The invention provides a novel green environmentally-friendly method to efficiently synthesize the sulfur sulfone derivatives, and one thioether compound and an oxidizing agent are subjected to direct oxidization to form one corresponding sulfur sulfone compound under illumination by utilizing cercosporin as a catalyst. The method provided by the invention adopts the cercosporin as the catalyst, the catalytic conditions are milder, the reaction can be performed at room temperature under visible light irradiation, the catalyst has high catalytic activity and can be used for high-selectivity catalytic synthesis of the sulfur sulfone compounds, and the micro catalyst can make a yield higher, wherein the yield can reach 90% or more; and the photocatalyst and substrate raw materials used in the method are simple and easy to obtain, have low costs and can be produced on a large scale, and the method has very good application prospects.

Description

technical field [0001] The invention belongs to the technical field of catalysis, and in particular relates to a method for photocatalytically synthesizing sulfur sulfone compounds. Background technique [0002] Thisulfone derivatives are effective building blocks for many organic compounds and drug candidates, and have exhibited many important biological activities. Given these importance, their synthesis has attracted great attention in the synthetic field. The most conventional method of synthesizing sulfones is through the oxidation of sulfides. This can be achieved by using stoichiometric amounts of acid or inorganic oxidizing agents, but these methods are atom-inefficient and produce contamination that is difficult to remove. Photocatalytic technology has mild reaction conditions, less catalyst consumption, energy saving and environmental protection, which has attracted widespread attention. Therefore, it is very necessary to develop green catalysts for the highly s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C315/02C07C317/14C07C317/10C07C317/22
Inventor 饶义剑李佳张艳包文豪
Owner JIANGNAN UNIV
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