4.4 Article

CuCl catalyzed selective oxidation of primary alcohols to carboxylic acids with tent-butyl hydroperoxide at room temperature

Journal

TETRAHEDRON LETTERS
Volume 49, Issue 15, Pages 2457-2460

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2008.02.031

Keywords

CuCl; alcohol oxidation; selective oxidation; carboxylic acid; benzylic alcohols

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Direct oxidation of primary alcohols to the corresponding carboxylic acids is performed highly efficiently at room temperature with anhydrous tort-butyl hydroperoxide in the presence of a catalytic amount of easily available CuCl under ligand free conditions in acetonitrile. Benzylic alcohols are more reactive than aliphatic alcohols, and these benzylic alcohols are selectively oxidized to the corresponding acids in the presence of aliphatic alcohols such as 1-octanol and 1-decanol. (C) 2008 Elsevier Ltd. All rights reserved.

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