Journal article
Mechanistic investigation of the gold-catalyzed aerobic oxidation of alcohols
Organic Chemistry, Department of Chemistry, Technical University of Denmark1
Department of Chemistry, Technical University of Denmark2
Department of Micro- and Nanotechnology, Technical University of Denmark3
Technical University of Denmark4
Centre for Catalysis and Sustainable Chemistry, Department of Chemistry, Technical University of Denmark5
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 (k(H)/k(D) = 1.41), when employing an alcohol substrate deuterated in this position.
Language: | English |
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Publisher: | Springer US |
Year: | 2008 |
Pages: | 184-190 |
ISSN: | 1572879x and 1011372x |
Types: | Journal article |
DOI: | 10.1007/s10562-007-9301-8 |
ORCIDs: | Fristrup, Peter |