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Org Lett. 2005 Oct 13;7(21):4549-52.

Bismuth-catalyzed benzylic oxidations with tert-butyl hydroperoxide.

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  • 1Department of Chemistry, Imperial College London, Exhibition Road, London SW7 2AZ, England.


[reaction: see text] 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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