Bismuth-catalyzed benzylic oxidations with tert-butyl hydroperoxide.
[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.
Bonvin
Yannick
Y
Department of Chemistry, Imperial College London, Exhibition Road, London SW7 2AZ, England.
Callens
Emmanuel
E
Larrosa
Igor
I
Henderson
David A
DA
Oldham
James
J
Burton
Andrew J
AJ
Barrett
Anthony G M
AG
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*
D001593:Benzyl Compounds; D020122:tert-Butylhydroperoxide; D001729:Bismuth