Aerobic Photooxidative Cleavage of Vicinal Diols to Carboxylic Acids Using 2-Chloroanthraquinone

Yoko Matsusaki, Tomoaki Yamaguchi, Norihiro Tada, Tsuyoshi Miura, Akichika Itoh*

*Gifu Pharmaceutical University, 1-25-4, Daigaku-nishi, Gifu 501-1196, Japan, Email: itohagifu-pu.ac.jp

Y. Matsusaki, T. Yamaguchi, N. Tada, T. Miura, A. Itoh, Synlett, 2012, 23, 2059-2062.

DOI: 10.1055/s-0032-1316585

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Abstract

An aerobic photooxidative cleavage of vicinal diols yields carboxylic acids using 2-chloroanthraquinone in the presence of photoirradiation with a high-pressure mercury lamp. This is a metal-free reaction in which molecular oxygen is used as the terminal oxidant.

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Catalytic Oxidative Cleavage of 1,3-Diketones to Carboxylic Acids by Aerobic Photooxidation with Iodine

N. Tada, M. Shomura, L. Cui, T. Nobuta, T. Miura, A. Itoh, Synlett, 2011, 2896-2900.

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Key Words

photooxidation, aerobic, anthraquinone, vicinal diol, carboxylic acid, oxidative cleavage, oxidation of alcohols

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ID: J60-Y2012-2770