Palladium-Catalyzed Cyanation of Aryl Sulfonium Salts

A palladium-catalyzed cyanation of aryl dimethylsulfoniumsaltsusing cheap, nontoxic, and bench-stable K-4[Fe-(CN)(6)]center dot 3H(2)O as the cyanating reagent has been developed.The reactions proceeded well under base-free conditions with varioussulfonium salts and provided aryl nitrile with yields of up to 92%.Aryl sulfides can be transformed to aryl nitriles directly via a one-potprocess, and the protocol is scalable. Density functional theory calculationswere performed to investigate the reaction mechanism that involveda catalytic cycle involving oxidative addition, ligand exchange, reductiveelimination, and regeneration to yield the product.