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Bioinspired o-Naphthoquinone-Catalyzed Aerobic Oxidation of Alcohols to Aldehydes and Ketones

Jisun Baek, Tengda Si, Hun Young Kim and Kyungsoo Oh*

*Center for Metareceptome Research, Graduate School of Pharmaceutical Sciences, Chung-Ang University, 84 Heukseok-ro, Dongjak, Seoul 06974, Republic of Korea, Email: kyungsooohcau.ac.kr

J. Baek, T. Si, H. Y. Kim, K. Oh, Org. Lett., 2022, 24, 4982-4986.

DOI: 10.1021/acs.orglett.2c02037


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Abstract

The use of an ortho-naphthoquinone catalyst enables a biomimetic alcohol dehydrogenase (ADH)-like oxidation protocol as green alternative to existing stoichiometric and metal-catalyzed alcohol oxidation reactions. The developed organocatalytic aerobic oxidation protocol proceeds through an intramolecular 1,5-hydrogen atom transfer of naphthalene alkoxide intermediates.

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proposed mechanism



Key Words

aldehydes, oxygen, organocatalysis, green chemistry


ID: J54-Y2022