Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 15, Pages 5156-5159Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201600549
Keywords
amines; catalysis; nitriles; organic chemistry; synthetic methods
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Funding
- Procter & Gamble Pharmaceuticals, Mason, OH
- University of Connecticut Office of Undergraduate Research
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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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