Study On Electrochemical Catalyzed β-iodovinyl Sulfone Reaction

The development of efficient and environmental protocol for the synthesis of privileged molecular skeletons has been a challenging task for synthetic chemists and is the focus of the modern organic chemistry.Among them,difunctionalization of alkynes represents an important contribution to the functionalized alkynes.Typically,the direct difunctionalization of alkynes could provide a straightforward method for achieving scaffold diversity in organic transformations.Alkyne iodosulfonylation is a powerful strategy for synthesizing β-iodovinyl sulfone compounds that are interesting for rapid construction of diverse functional groups in biologically active molecules.The traditional synthesis of this kind of combination requires a large number of oxidants or metal catalysts,which has a certain impact on the environment to some extent.Herein,an electrochemically catalyzed green synthesis method of β-iodoalkenyl sulfone has been disclosed in this article.Through electrochemical method,this article uses alkynes and sulfonyl hydrazine as the reaction substrate and Na I as iodine source,which utilizes the working principle of the electrolytic cell,that is,the gains and losses of electrons involved in the electrolysis process,avoiding the use of oxidants.By studying the universality of the reaction,aryl,alkyl alkynes and various sulfonyl hydrazides can all react under this condition to synthesize a series of highly selective β-iodenyl sulfone compounds with rapid reaction efficiency and mild condition,and capable of gram preparation.Moreover,the proposed method has high regioselectivity and stereoselectivity.At the same time,it is the first time to obtain the coupling product of bis-substituted arylsulfonohydrazides.By studying the mechanism,it is speculated that the reaction is a free radical reaction.