Selective Aerobic Oxidation of Primary Alcohols to Aldehydes

Masatoshi Shibuya*, Keisuke Furukawa, Yoshihiko Yamamoto

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

M. Shibuya, K. Furukawa, Y. Yamamoto, Synlett, 2017, 28, 1554-1557.

DOI: 10.1055/s-0036-1588155

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Abstract

The use of tert-butyl nitrite as the co-catalyst in a 2-azaadamantane-N-oxyl (AZADO)- and 9-azanoradamantane-N-oxyl (nor-AZADO)-catalyzed efficient aerobic oxidation of primary alcohols in MeCN instead of the previously reported AcOH provides the corresponding aldehydes selectively. The addition of saturated aqueous NaHCO₃ after the completion of the reaction suppresses the overoxidation of the product during the workup.

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Key Words

oxidation, nitroxyl radical, AZADO, Nor-AZADO, tert-butyl nitrite, organocatalysis, primary alcohols, aldehydes, chemoselectivity, air

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ID: J60-Y2017