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Catalytic Aerobic Oxidation of Alcohols using Recoverable IAPNO [alpha]-Hydrogen Nitroxyl Radicals

ChemCatChem, 2015-04, Vol.7 (7), p.1129 [Peer Reviewed Journal]

ISSN: 1867-3880 ;EISSN: 1867-3899 ;DOI: 10.1002/cctc.201402985

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  • Title:
    Catalytic Aerobic Oxidation of Alcohols using Recoverable IAPNO [alpha]-Hydrogen Nitroxyl Radicals
  • Author: Bar, Sukanta ; Kumar, Jayprakash N ; Amar, Michal ; Toledo, Hila ; Batrice, Rami J ; Szpilman, Alex M
  • Subjects: Oxidation
  • Is Part Of: ChemCatChem, 2015-04, Vol.7 (7), p.1129
  • Description:   [alpha]-Hydrogen-substituted nitroxyl radicals are of considerable interest as catalysts for oxidation and polymerization, but are usually inherently unstable. We report herein the catalytic activity of a new family of stable iso-azaphenalene (IAPNO) [alpha]-hydrogen nitroxyl radicals in the copper/bipyridine/N-methylimidazole co-catalyzed aerobic oxidation of alcohols. The nitroxyl radical Mes/TIPSO-IAPNO (TIPSO=triisopropyloxy, IAPNO=isoazaphenalene N-oxyl) displays higher activity than TEMPO in the oxidation of benzylic and allylic alcohols. Alkyl, benzyl, allyl, and propargyl alcohols are oxidized with yields up to 96%. The readily prepared nitroxyl catalysts are recovered in 75-90% yield after purification of the reaction mixture and are recycled.
  • Publisher: Weinheim: Wiley Subscription Services, Inc
  • Language: English
  • Identifier: ISSN: 1867-3880
    EISSN: 1867-3899
    DOI: 10.1002/cctc.201402985
  • Source: Alma/SFX Local Collection
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