Base-promoted efficient transformation of aryl methylene bromides and DMSO to vinyl sulfoxides

Abstract

Sulfoxides and their derivatives have attracted considerable attention due to their extensive applications in both medicinal and organic chemistry, serving as versatile chiral auxiliaries or ligands in transition-metal catalysis and as fundamental building blocks in organic synthesis. Herein, we report the development of an efficient tandem reaction for the chemoselective synthesis of vinyl sulfoxides from aryl methylene bromides and DMSO, which serves simultaneously as an oxidant, substrate, and solvent. This innovative method involves sequential Kornblum oxidation of bromide compounds to produce the corresponding aldehydes, which subsequently undergo base-promoted condensation with DMSO. The reaction shows remarkable tolerance for a variety of functional groups on the phenyl ring, and notably, 2-(bromomethyl)naphthalene is also shown to be a compatible substrate, further extending the scope of this methodology.