Bismuth-Catalyzed Benzylic Oxidations with tert-Butyl Hydroperoxide

Bismuth-Catalyzed Benzylic Oxidations with tert-Butyl Hydroperoxide

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%). Preliminar...

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Veröffentlicht in:Organic letters 2005-10, Vol.7 (21), p.4549-4552
Hauptverfasser: Bonvin, Yannick, Callens, Emmanuel, Larrosa, Igor, Henderson, David A, Oldham, James, Burton, Andrew J, Barrett, Anthony G. M
Format: Artikel
Sprache:eng
Schlagworte:
Benzyl Compounds - chemistry
Bismuth - chemistry
Catalysis
Hydrogen Bonding
Molecular Structure
Oxidation-Reduction
tert-Butylhydroperoxide - chemistry
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Beschreibung
Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol051765k