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2-Azaadamantane N-Oxyl (AZADO) and 1-Me-AZADO:  Highly Efficient Organocatalysts for Oxidation of Alcohols

Masatoshi Shibuya, Masaki Tomizawa, Iwao Suzuki and Yoshiharu Iwabuchi*

*Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aobayama, Sendai 980-8578, Japan, Email: y-iwabuchim.tohoku.ac.jp

M. Shibuya, M. Tomizawa, I. Suzuki, Y. Iwabuchi, J. Am. Chem. Soc., 2006, 128, 8412-8413.

DOI: 10.1021/ja0620336 (free Supporting Information)


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Abstract

A stable nitroxyl radical class of catalysts, 2-azaadamantane N-oxyl (AZADO) and 1-Me-AZADO, exhibit superior catalytic proficiency to TEMPO, converting various sterically hindered alcohols to the corresponding carbonyl compounds in excellent yields.

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Organocatalytic One-Pot Oxidative Cleavage of Terminal Diols to Dehomologated Carboxylic Acids

M. Shibuya, R. Doi, T. Shibuta, S.-i. Uesugi, Y. Iwabuchi, Org. Lett., 2012, 14, 5006-5009.


Key Words

AZADO, TEMPO, bleach, synthesis of ketones, Organocatalysis


ID: J48-Y2006-4920