A Palladium-Catalyzed Multicascade Reaction: Facile Low-Temperature Hydrogenolysis of Activated Nitriles and Related Functional Groups

The facile hydrogenolysis of various nitriles, imines, and amines over Pd/C has been achieved by using straightforward and relatively mild conditions. Substrates that contain an aryl group adjacent to the nitrogen-containing functionality were hydrogenolyzed most effectively. The stabilization of the proposed eta(2)-coordinated palladium intermediate by this group was partly responsible for this observation and is borne out by ab initio calculations.