Palladium-Catalyzed Regio- and Stereoselective Coupling–Addition of Propiolates with Arylsulfonyl Hydrazides: A Pattern for Difunctionalization of Alkynes

Abstract

A new pattern for difunctionalization of alkynes via a palladium-catalyzed regio- and stereoselective coupling-addition of propiolates with arylsulfonyl hydrazides is disclosed. The approach enables the synthesis of various highly functionalized ( E)-vinylsulfones in satisfactory yields. Arylsulfonyl hydrazides act as both aryl and sulfonyl sources via selective cleavage of Ar(C)-S and S-N bonds, which are simultaneously incorporated onto the terminal carbon atom of an alkyne molecule.