Copper(II)-Catalyzed Chemo- and Stereocontrolled Synthesis of (E)-Vinyl Sulfones and (Z)-β-Chlorovinyl Sulfones from Terminal Alkynes and Arylsulfonyl Hydrazides

Abstract

A facile copper(II)-catalyzed regio- and stereocontrolled synthesis of vinyl sulfones from terminal alkynes and arylsulfonyl hydrazides is described. Depending on the source of copper(II), two different kinds of vinyl sulfones, (E)-vinyl sulfones and (Z)-β-chlorovinyl sulfones were obtained and the addition of cyclohexanone played an important role in the reaction. These reactions display excellent chemoselectivity as well as stereoselectivity.

Key words

copper(II) - catalysis - vinyl sulfones - terminal alkynes - arylsulfonyl hydrazides - cyclohexanone - chemoselectivity - stereoselectivity

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