Journal
CHEMICAL REVIEWS
Volume 118, Issue 9, Pages 4834-4885Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.chemrev.7b00763
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Funding
- Center for Molecular Electrocatalysis, as an Energy Frontier Research Center - U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences
- NIH [R01 GM100143]
- Great Lakes Bioenergy Research Center (DOE BER Office of Science) [DE-FC02-07ER64494]
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM100143] Funding Source: NIH RePORTER
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N-Oxyl compounds represent a diverse group of reagents that find widespread use as catalysts for the selective oxidation of organic molecules in both laboratory and industrial applications. While turnover of N-oxyl catalysts in oxidation reactions may be accomplished with a variety of stoichiometric oxidants, N-oxyl reagents have also been extensively used as catalysts under electrochemical conditions in the absence of chemical oxidants. Several classes of N-oxyl compounds undergo facile redox reactions at electrode surfaces, enabling them to mediate a wide range of electrosynthetic reactions. Electrochemical studies also provide insights into the structural properties and mechanisms of chemical and electrochemical catalysis by N-oxyl compounds. This review provides a comprehensive survey of the electrochemical properties and electrocatalytic applications of aminoxyls, imidoxyls, and related reagents, of which the two prototypical and widely used examples are 2,2,6,6-tetramethylpiperidine N-oxyl (TEMPO) and phthalimide N-oxyl (PINO).
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