Chemistry: A European Journal 2016-04-04

Metal-Free Oxidation of Primary Amines to Nitriles through Coupled Catalytic Cycles.

Kyle M Lambert, James M Bobbitt, Sherif A Eldirany, Liam E Kissane, Rose K Sheridan, Zachary D Stempel, Francis H Sternberg, William F Bailey

Index: Chemistry 22(15) , 5156-9, (2016)

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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.© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.