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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 (free Supporting Information)


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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


ID: J60-Y2017