Copper acetate mediated thiomethylation of 2-pyridine-substituted acrylonitriles with DMSO

Abstract

An efficient synthesis of a variety of alkenyl methyl thioethers from acrylonitriles and dimethyl sulfoxide is described. This copper acetate mediated thiomethylation reaction provides the corresponding products with broad substrate scope in moderate to excellent yields. This transformation is achieved through direct functionalization of vinylic C–H bonds, resulting in stereospecific formation of the formal cyanothiolation product of internal alkynes.