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Bismuth-Catalyzed Benzylic Oxidations with tert-Butyl Hydroperoxide

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, Email:

Y. Bonvin, E. Callens, I. Larrosa, D. A. Henderson, J. Oldham, A. J. Burton, A. G. M. Barrett, Org. Lett., 2005, 7, 4549-4552.

DOI: 10.1021/ol051765k

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The bismuth and picolinic acid-catalyzed oxidation of alkyl arenes with tert-butyl hydroperoxide in pyridine and acetic acid gave benzylic ketones in good yields. Alternatively, oxidation of methyl arenes gave the corresponding substituted benzoic acids. A radical mechanism is discussed.

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Key Words

tert-butyl hydroperoxide, Ketones

ID: J54-Y2005-1600