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Copper-catalyzed Difluoroalkylation-thiolation Of Alkenes

Posted on:2022-01-13Degree:MasterType:Thesis
Country:ChinaCandidate:Y J NiFull Text:PDF
GTID:2491306740468804Subject:Chemistry
Abstract/Summary:
The framwork of fluoroalkylation thiolation products of alkenes plays an important role in drugs and natural products.The exploration of synthetic methods for such framwork compounds has great application prospects.The synthetic methods reported in recent years for such compounds usually require expensive with the participation of iridium catalysts,low-cost catalysts to achieve this type of reaction have high development value,but there are few reports.This article focuses on the transition metal copper-catalyzed difluoroalkylation-thiolation of alkenes.This paper mainly includes the following four aspects of work:1.Developed a copper-catalyzed difluoroalkylation-thiolation of alkenes.This reaction uses styrene as the reaction substrate,p-toluene disulfide as the sulfur source,difluoro ethyl bromoacetate as the difluoroalkyl source,and cuprous chloride and sodium metabisulfite as the catalytic system to successfully obtain the alkene difluoroalkylation-thiolation products.2.The reaction temperature,catalysts,reducing agents,additives,solvents,time,and other factors affecting the reaction were optimized to obtain the best reaction conditions.3.The scope of application of the reaction was investigated.A variety of alkenes and disulfides can show good substrate tolerance,aliphatic alkenes and natural product active structures aryl alkenes are also suitable,and the resulting products can undergo different types of subsequent conversions.4.The reaction mechanism was explored,and a possible radical reaction mechanism was proposed.In conclusion,this paper has developed a novel copper-catalyzed difluoroalkylationthiolation of alkenes method.Compared with the reported work,it avoids the use of expensive iridium catalysts and organoboron reagents.The reaction operation method is simple and the reaction conditions Gentle and efficient,the highest yield can reach 91%.This method promotes the research of low-cost transition metal catalyzed difluoroalkylationthiolation of alkenes,and at the same time provides an effective method for the synthesis of this type of compound,which has potential application value.
Keywords/Search Tags:alkenes, difluoroalkylation-thiolation, copper-catalyzed, Sodium metabisulfite, Multicomponent reactions
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