Cu/Nitroxyl-Catalyzed Aerobic Oxidation of Primary Amines into Nitriles at Room Temperature

Abstract

An efficient catalytic method has been developed for aerobic oxidation of primary amines to the corresponding nitriles. The reactions proceed at room temperature and employ a catalyst consisting of (4,4'- <i>^t</i> Bu₂bpy)CuI/ABNO (ABNO = 9-azabicyclo[3.3.1]nonan-3-one <i>N</i>-oxyl). The reactions exhibit excellent functional group compatibility and substrate scope, and are effective with benzylic, allylic and aliphatic amines. Preliminary mechanistic studies suggest that aerobic oxidation of the Cu catalyst is the turnover-limiting step of the reaction.