Catalysis Letters

, Volume 120, Issue 3, pp 184–190

Mechanistic Investigation of the Gold-catalyzed Aerobic Oxidation of Alcohols

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

DOI: 10.1007/s10562-007-9301-8

Cite this article as:
Fristrup, P., Johansen, L.B. & Christensen, C.H. Catal Lett (2008) 120: 184. doi:10.1007/s10562-007-9301-8

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 catalysisOxidationsGoldMechanismHammett

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