Metal-Free Oxidation of Primary Amines to Nitriles through Coupled Catalytic Cycles
Kyle M Lambert1, James M Bobbitt1, Sherif A Eldirany1
1Department of Chemistry, University of Connecticut, 55 North Eagleville Rd, Storrs, CT, 06269-3060, USA.
Abstract:
Synergism among several intertwined catalytic cycles allows for selective, room temperature oxidation of primary amines to the corresponding nitriles in 85-98% isolated yield. This metal-free, scalable, operationally simple method employs a catalytic quantity of 4-acetamido-TEMPO (ACT; TEMPO=2,2,6,6-tetramethylpiperidine N-oxide) radical and the inexpensive, environmentally benign triple salt oxone as the terminal oxidant under mild conditions. Simple filtration of the reaction mixture through silica gel affords pure nitrile products.
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