Mechanistic Investigation of the Gold-catalyzed Aerobic Oxidation of Alcohols
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- Fristrup, P., Johansen, L.B. & Christensen, C.H. Catal Lett (2008) 120: 184. doi:10.1007/s10562-007-9301-8
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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.