One-Pot, Three-Component Assembly of Sulfides Using a Sulfoxide Reagent as a Sulfur Dication Equivalent

Abstract

We report a one-pot, three-component synthesis of sulfides by exploiting a sulfoxide reagent as a formal sulfur dication equivalent. Our protocol consists of three simple chemical operations involving two Grignard reagents and trimethylsilyl chloride (TMSCl) to sequentially form sulfenate anions, sulfenate esters, and sulfides. We demonstrate a wide range of Grignard reagents to be coupled, thereby allowing the modular, thiol-free synthesis of sulfides including dialkenyl and alkenyl–alkynyl sulfides.