Aryl sulfoxide, thioether compound, synthesis method and application thereof

Abstract

The invention discloses a method for selective synthesis of an aryl sulfoxide compound (III) and an aryl thioether compound (IV). According to the invention, in a reactive solvent, an aryl high iodinesalt is adopted as the reaction raw material, aryl / alkyl thiosulfate is taken as the vulcanizing reagent, under the catalysis of visible light and a photosensitive reagent, and under the action of lewis acid and alkali, when the reaction atmosphere is nitrogen, the thioether compound (IV) can be generated, and when the reaction atmosphere is air, the sulfoxide compound (III) can be generated. Thesynthesis method provided by the invention has the advantages of easily available and cheap raw materials, simple reaction operation, mild and environment-friendly reaction conditions, high yield, and excellent functional group tolerance. The invention also discloses the new aryl sulfoxide compound (III) and aryl thioether compound (IV), also successfully realizes later modification of drugs andsugar, and realizes the formal synthesis of some drugs, and provides an efficient method for selective construction of thioether and sulfoxide compounds.

Description

technical field [0001] The invention belongs to the technical field of organic compound technology application, and specifically relates to a class of aryl sulfoxide and sulfide compounds and a synthesis method thereof. Background technique [0002] Aryl sulfoxides and thioether compounds are two very important compounds, which widely exist in various drug molecules and natural products, and in the process of drug development, sulfur-containing compounds in various oxidation states are generally studied at the same time, because they contain similar Compounds with different oxidation states of the skeleton may all be active molecules, and may also target diseases of different subspecies. Therefore, it is particularly important to selectively construct sulfoxides and thioethers from some simple and commercially available raw materials. [0003] [0004] The traditional method of synthesizing aryl sulfide compounds is mainly through the preparation of thiol or thiophenol c...

AI Technical Summary

Problems solved by technology

In this type of method, the organic sulfur used is easily oxidized and has a toxic effect on metal catalysts; the raw materials have a strong taste and are harmful to the environment and human body to varying degrees; the raw materials are relatively expensive, and complex substrates need to be pre-prepared; Many of the above deficiencies restrict the in-depth application of such methods in the field of process research and medicinal chemistry research.

Moreover, the synthesis of traditional aryl sulfide compounds needs to be carried out under high temperature conditions, which consumes a lot of energy, does not conform to the development trend of green chemistry, and restricts the large-scale application of such methods in industry

Sulfoxide compounds are produced by oxidizing sulfide compounds. The oxidants required are generally peroxides or high-oxidation compounds, which have poor atom economy, large pollution, and are relatively dangerous.

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