Nickel-Catalyzed Synthesis of an Aryl Nitrile via Aryl Exchange between an Aromatic Amide and a Simple Nitrile

Herein, a nickel-catalyzed synthesis of an aryl nitrilevia aryl exchange between an aromatic amide and a simple nitrilewas developed. By using cheap, easy-to-handle, and low-toxic 4-cyanopyridine as the cyanating source, cyanation of variousaromatic amides afforded an assortment of aryl nitriles includingbioactive drugs and organic luminescent molecules in good yields.The reaction exhibited wide substrate scope, good functionalgroup tolerance, and unique selectivity that were complementaryto traditional methods. Moreover, two key nickel complexesformed by oxidative addition to each substrate are obtained anddetermined by X-ray crystallography, which gave strong supportfor the mechanism elucidations.