Palladium-catalyzed cyanation of aryl (pseudo)halides using a redox-active N–CN reagent

An efficient palladium-catalyzed cyanation of aryl bromides has been demonstrated using a readily accessible and redox-active electrophilic cyanating reagent. The reaction was successfully extended to the cyanation of aryl iodides, triflates, and diazonium salts. Various functionalized aryl nitriles and drug intermediates were achieved in good to excellent yields. Important features of this reaction include wide functional group tolerance, a broad substrate scope, and a reductant-free approach. The preliminary mechanistic investigation and identification of oxidized imine supported the proposed plausible reaction mechanism.