Bismuth-catalyzed benzylic oxidations with tert-butyl hydroperoxide

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Abstract

(Chemical Equation Presented) 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 benzole acids (50-95%). Preliminary mechanistic studies were consistent with a radical mechanism rather than a bismuth(III)-bismuth(V) cycle. © 2005 American Chemical Society.

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Bonvin, Y., Callens, E., Larrosa, I., Henderson, D. A., Oldham, J., Burton, A. J., & Barrett, A. G. M. (2005). Bismuth-catalyzed benzylic oxidations with tert-butyl hydroperoxide. Organic Letters, 7(21), 4549–4552. https://doi.org/10.1021/ol051765k

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