A Thiol-Ene-Based Synthesis Of ?-deuterated Sulfide Compounds

Sulfide compounds are widely found in pesticide,pharmaceuticals and material,which possess a crucial application value.Among many methods for synthesizing sulfide compounds,Thiol-Ene reaction has attracted widespread attention due to the advantages of high atomic economy and easy availability of starting materials.Metal-catalyzed and non-metal-catalyzed Thiol-Ene reactions can already achieve the conversion of various alkyl mercaptans or thiophenols with olefins.The recently developed photocatalytic strategies can also obtain the products of Thiol-Ene reaction under mild conditions.With the development of deuterated drugs,the synthesis of deuterated sulfide compounds has become a new research hotspot in the field of drug research.However,the current strategies for synthesizing deuterated sulfide compounds have the disadvantages of expensive deuterium sources and complicated operations.In this paper,we combined the Thiol-Ene reaction with D2O,and a series of ?-deuterated sulfide was synthesized under mild conditions.The paper will be introduced by two parts:Part ? The applications of sulfide compounds and the research of Thiol-Ene reaction were reviewed.Part ? Introduction of this work:We have obtained a series of deuterated sulfide through Thiol-Ene reaction,which was used D2O as the deuterium source.First,we have optimized the reaction conditions by using p-methoxystyrene and p-methoxythiophenol as model substrates and the best reaction conditions was found finally.Second,we have investigated the applicability of the substrates.A variety of substituted thiophenols and styrenes as well as ?,?-unsaturated ketones,aldehydes,esters,amides,and cyano-substituted olefins smoothly underwent the reaction to generate ?-deuterated aryl sulfide in excellent yields and D content.In addition,derivatives of natural products can also participate in the reaction with good results,and the product can also be prepared on a gram scale.Finally,free radical capture experiments and EPR reactions are conducted to exploring the mechanism of this reaction.A proposed mechanism is proposed.