Gold-Catalyzed Redox-Neutral Reaction of Nitriles with Quinoline N-Oxides

A method for the redox-neutral reaction of nitriles with quinoline N-oxides via gold catalysis is described. This transformation features a broad substrate scope and good functional group tolerance. A series of C2-amidated quinolines were synthesized in good to excellent yields under mild reaction conditions. Mechanistic studies suggested that the oxidative gold catalysis of nitriles might be initiated by the & sigma;-coordination of the gold catalyst with the N atom on nitrile, then the coordinated gold-nitrile intermediate is captured and oxidized by quinoline N-oxides.