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 nitrile via aryl exchange between an aromatic amide and a simple nitrile was developed. By using cheap, easy-to-handle, and low-toxic 4-cyanopyridine as the cyanating source, cyanation of various aromatic amides afforded an assortment of aryl nitriles including bioactive drugs and organic luminescent molecules in good yields. The reaction exhibited wide substrate scope, good functional group tolerance, and unique selectivity that were complementary to traditional methods. Moreover, two key nickel complexes formed by oxidative addition to each substrate are obtained and determined by X-ray crystallography, which gave strong support for the mechanism elucidations.