Nitriles are important functional groups and useful intermediates in synthetic chemistry. Conventional methods for the preparation of nitriles often use cyanide as a toxic reagent or required high reaction temperatures. This presentation will describe a very mild method for the preparation of nitriles via metal-catalyzed oxidative dehydrogenation of primary amines with molecular oxygen as the stoichiometric oxidant. The method is effect for benzylic, allylic and aliphatic amines and exhibits broad functional group tolerance. This work builds on our recently reported method for chemoselective oxidation of primary alcohols with a (bpy)Cu/TEMPO catalyst system. Optimization of the identity of the homogeneous copper and nitroxyl cocatalysts enables highly efficient amine oxidation.

Cu/nitroxyl-catalyzed aerobic oxidation of primary amines to nitriles at room temperature

246th National Meeting (2013)

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