title: Bismuth-catalyzed benzylic oxidations with tert-butyl hydroperoxide.
abstract: [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.
authors.affiliation: Department of Chemistry, Imperial College London, Exhibition Road, London SW7 2AZ, England.
authors.forename: Yannick
authors.initials: Y
authors.lastname: Bonvin
authors.forename: Emmanuel
authors.initials: E
authors.lastname: Callens
authors.forename: Igor
authors.initials: I
authors.lastname: Larrosa
authors.forename: David A
authors.initials: DA
authors.lastname: Henderson
authors.forename: James
authors.initials: J
authors.lastname: Oldham
authors.forename: Andrew J
authors.initials: AJ
authors.lastname: Burton
authors.forename: Anthony G M
authors.initials: AG
authors.lastname: Barrett
mesh_terms: D001593:Benzyl Compounds / Q000737:chemistry*; D001729:Bismuth / Q000737:chemistry*; D002384:Catalysis; D006860:Hydrogen Bonding; D015394:Molecular Structure; D010084:Oxidation-Reduction; D020122:tert-Butylhydroperoxide / Q000737:chemistry*
chemical_list: D001593:Benzyl Compounds; D020122:tert-Butylhydroperoxide; D001729:Bismuth