A Very Mild and Chemoselective Oxidation of Alcohols to Carbonyl Compounds

Lidia De Luca, Giampaolo Giacomelli and Andrea Porcheddu

*Dipartimento di Chimica, Università degli Studi di Sassari, via Vienna 2, I-07100 Sassari, Italy

L. De Luca, G. Giacomelli, A. Porcheddu, Org. Lett., 2001, 3, 3041-3043.

DOI: 10.1021/ol016501m

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Abstract

An efficient oxidation of primary alcohols to the corresponding aldehydes can be carried out at room temperature in DCM, using trichloroisocyanuric acid in the presence of catalytic TEMPO:  aliphatic, benzylic, and allylic alcohols, and β-amino alcohols are rapidly oxidized without no overoxidation to carboxylic acids. The slow oxidation of secondary carbinols makes the reaction highly chemoselective.

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Key Words

Aldehydes, Ketones, TEMPO, Trichloroisocyanuric Acid

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ID: J54-Y2001