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■ The Utility of Oxoammonium Species in Organic Synthesis: Beyond Alcohol Oxidation

Shota Nagasawa, Yusuke Sasano, and Yoshiharu Iwabuchi*

*Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3, Aoba, Aramaki, Aoba-ku, Sendai, 980-8578, Japan

Abstract

Oxoammonium species are electrophilic chemical species generated via single electron oxidation of nitroxyl radicals. Although this species and its salts are known as useful oxidants and active species for (catalytic) oxidation of alcohols into carbonyl compounds in organic synthesis, the benefits of oxoammonium species for the oxidative transformations of numerous types of substrates apart from alcohols has been reported. This review summarizes the synthetic utility of oxoammonium species under both stoichiometric and catalytic conditions with the exception of alcohol oxidation.