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Chemoselective Catalytic α-Oxidation of Carboxylic Acids: Iron/Alkali Metal Cooperative Redox Active Catalysis

Tsukushi Tanaka, Ryo Yazaki* and Takashi Ohshima*

*Graduate School of Pharmaceutical Sciences, Kyushu University, Maidashi, Higashi-ku, Fukuoka 812-8582, Japan, Email:,

T. Tanaka, R. Yazaki, T. Ohshima, J. Am. Chem. Soc., 2020, 142, 4517-4524.

DOI: 10.1021/jacs.0c00727

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α-Oxidation of a variety of carboxylic acids, which preferentially undergo undesired decarboxylation under radical conditions, proceeded efficiently under optimized conditions via a chemoselective enolization without stoichiometric amounts of Brønsted base. The formed redox-active heterobimetallic enediolate efficiently coupled with free radical TEMPO.

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Key Words

α-hydroxylation, TEMPO

ID: J48-Y2020