Palladium-Catalyzed Cyanation of Aryl Sulfonium Salts

Abstract

A palladium-catalyzed cyanation of aryl dimethylsulfonium salts using cheap, nontoxic, and bench-stable K₄[Fe(CN)₆]·3H₂O as the cyanating reagent has been developed. The reactions proceeded well under base-free conditions with various sulfonium salts and provided aryl nitrile with yields of up to 92%. Aryl sulfides can be transformed to aryl nitriles directly via a one-pot process, and the protocol is scalable. Density functional theory calculations were performed to investigate the reaction mechanism that involved a catalytic cycle involving oxidative addition, ligand exchange, reductive elimination, and regeneration to yield the product.