In situ Formation of NO_x and Br Anion for Aerobic Oxidation of Benzylic Alcohols without Transition Metal

Guanyu Yang*, Wei Wang, Weimin Zhu, Cunbin An, Xinqin Gao, Maoping Song*

*Department of Chemistry, Zhengzhou University, 75 Daxue Road, Zhengzhou 450052, P. R. of China, Email: yangguanyuzzu.edu.cn, mpsong9350zzu.edu.cn

G. Yang, W. Wang, W. Zhu, C. An, X. Gao, M. Song, Synlett, 2010, 437-440.

DOI: 10.1055/s-0029-1219202

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Abstract

The reaction of KBrO₃ and NH₂OH • HCl in situ generates NO_x and Br anion, which allows in the presence of 2,2,6,6-tetramethylpiperidine-N-oxide (TEMPO) an activation of dioxygen to oxidize various benzylic alcohols quantitatively to their corresponding carbonyl compounds under mild conditions.

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Key Words

oxidation, alcohols, aldehydes, catalyst, bromate, hydroxylammonium, 2,2,6,6-tetramethylpiperidine-N-oxide, oxygen

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ID: J60-Y2010-0460