Chemoselective Catalytic Oxidation of 1,2-Diols to α-Hydroxy Acids Controlled by TEMPO-ClO₂ Charge-Transfer Complex

Keisuke Furukawa, Masatoshi Shibuya* and Yoshihiko Yamamoto

*Department of Basic Medicinal Sciences, Graduate School of Pharmaceutical Sciences, Nagoya University, Furo-cho, Chikusa, Nagoya 464-8601, Japan, Email: m-shibups.nagoya-u.ac.jp

K. Furukawa, M. Shibuya, Y. Yamamoto, Org. Lett., 2015, 17, 2282-2285.

DOI: 10.1021/acs.orglett.5b01003

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Abstract

Catalytic amounts of TEMPO and NaOCl enable a chemoselective oxidation of 1,2-diols to in the presence of NaClO₂ as terminal oxidant. The use of a two-phase condition suppresses the concomitant oxidative cleavage. The observed selectivity seems to be derived from the precise solubility control of diols and hydroxy acids as well as the charge transfer complex TEMPO-ClO₂, which dissolves into the organic layer.

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Key Words

carboxylic acids, sodium chlorite, TEMPO

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ID: J54-Y2015