Efficient Oxidation of Alcohols to Carbonyl Compounds with Molecular Oxygen Catalyzed by N-Hydroxyphthalimide Combined with a Co Species

Takahiro Iwahama, Yasushi Yoshino, Takashi Keitoku, Satoshi Sakaguchi and Yasutaka Ishii*

*Department of Applied Chemistry, Faculty of Engineering & High Technology Research Center, Kansai University, Suita Osaka 564-8680, Japan

T. Iwahama, Y. Yoshino, T. Keitoku, S. Sakaguchi, Y. Ishii, J. Org. Chem., 2000, 65, 6502-6507.

DOI: 10.1021/jo000760s

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Abstract

The combination of N-hydroxyphthalimide (NHPI), a Co species, and optionally a small amount of a (per)benzoic acid catalyzes highly efficient oxidations of alcohols with oxygen. Primary alcohols are rapidly oxidized to the corresponding carboxylic acids, terminal vic-diols give one carbon less carboxylic acids, while internal vic-diols were selectively oxidized to 1,2-diketones.

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Key Words

ketones, carboxylic acids (hydrolysis, oxidation), oxygen

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ID: J42-Y2000