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Letter

Bismuth-Catalyzed Benzylic Oxidations with tert-Butyl Hydroperoxide

Supporting Info

Yannick Bonvin,^† Emmanuel Callens,^† Igor Larrosa,^† David A. Henderson,^† James Oldham,^† Andrew J. Burton,^‡ and Anthony G. M. Barrett*^†

Department of Chemistry, Imperial College London, Exhibition Road, London SW7 2AZ, England, and Chemical Development, GlaxoSmithKline, Medicines Research Centre, Stevenage SG1 2NY, England

Org. Lett., 2005, 7 (21), pp 4549–4552

DOI: 10.1021/ol051765k

Publication Date (Web): September 16, 2005

†

Imperial College London.

‡

GlaxoSmithKline.

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, agmb@imperial.ac.uk

Abstract

Oxidation of alkyl and cycloalkyl arenes with tert-butyl hydroperoxide catalyzed by bismuth and picolinic acid in pyridine and acetic acid gave the corresponding benzylic ketones (48−99%). Alternatively, oxidation of methyl arenes gave the corresponding substituted benzoic acids (50−95%). Preliminary mechanistic studies were consistent with a radical mechanism rather than a bismuth(III)−bismuth(V) cycle.

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Published In Issue October 13, 2005
Received July 26, 2005

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Letter

Bismuth-Catalyzed Benzylic Oxidations with tert-Butyl Hydroperoxide