Catalysis Letters

, Volume 120, Issue 3–4, pp 184–190

Mechanistic Investigation of the Gold-catalyzed Aerobic Oxidation of Alcohols

  • Peter Fristrup
  • Louise Bahn Johansen
  • Claus Hviid Christensen
Article

Abstract

The mechanism for the gold-catalyzed aerobic oxidation of alcohols was studied using a series of para-substituted benzyl alcohols (Hammett methodology). The competition experiments clearly show that the rate-determining step of the reaction involves the generation of a partial positive charge in the benzylic position (i.e. hydride abstraction). This was further substantiated by the determination of a significant kinetic isotope effect (kH/kD = 1.41), when employing an alcohol substrate deuterated in this position.

Keywords

Heterogeneous catalysis Oxidations Gold Mechanism Hammett 

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Copyright information

© Springer Science+Business Media, LLC 2007

Authors and Affiliations

  • Peter Fristrup
    • 1
  • Louise Bahn Johansen
    • 1
  • Claus Hviid Christensen
    • 1
  1. 1.Center for Sustainable and Green ChemistryTechnical University of DenmarkLyngbyDenmark

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