TEMPO/NBu₄Br-Catalyzed Selective Alcohol Oxidation with Periodic Acid

Mariam Attoui, Jean-Michel Vatèle*

*Université Lyon 1, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (ICBMS), bât. Raulin, 43, Bd du 11 Novembre 1918, 69622 Villeurbanne Cedex, France, Email: vateleuniv-lyon1.fr

M. Attoui, J.-M. Vatèle, Synlett, 2014, 25, 2923-2927.

DOI: 10.1055/s-0034-1378913

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Abstract

Oxidation of primary and secondary alcohols, using catalytic amounts of TEMPO and tetra-n-butylammonium bromide in combination with periodic acid and wet alumina in dichloromethane is compatible with a broad range of functional groups and acid-sensitive protecting groups. The system also enables a chemoselective oxidation of secondary alcohols in the presence of primary alcohols.

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Key Words

aldehydes, ketones, chemoselectivity, oxidation, periodic acid, TEMPO

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ID: J60-Y2014