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One-Pot Direct Oxidation of Primary Amines to Carboxylic Acids through Tandem ortho-Naphthoquinone-Catalyzed and TBHP-Promoted Oxidation Sequence
Authors:Dr Tengda Si  Prof Hun Young Kim  Prof Kyungsoo Oh
Institution:1. Center for Metareceptome Research, Graduate School of Pharmaceutical Sciences, Chung-Ang University, 84 Heukseok-ro, Dongjak, Seoul, 06974 Republic of Korea;2. Department of Global Innovative Drugs, Chung-Ang University, 84 Heukseok-ro, Dongjak, Seoul, 06974 Republic of Korea
Abstract:Biomimetic oxidation of primary amines to carboxylic acids has been developed where the copper-containing amine oxidase (CuAO)-like o-NQ-catalyzed aerobic oxidation was combined with the aldehyde dehydrogenase (ALDH)-like TBHP-mediated imine oxidation protocol. Notably, the current tandem oxidation strategy provides a new mechanistic insight into the imine intermediate and the seemingly simple TBHP-mediated oxidation pathways of imines. The developed metal-free amine oxidation protocol allows the use of molecular oxygen and TBHP, safe forms of oxidant that may appeal to the industrial application.
Keywords:aerobic oxidation  aldehyde  amine  carboxylic acid  TBHP
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