Oppenauer Oxidation

The aluminium-catalyzed hydride shift from the α-carbon of an alcohol component to the carbonyl carbon of a second component, which proceeds over a six-membered transition state, is named Meerwein-Ponndorf-Verley-Reduction (MPV) or Oppenauer Oxidation (OPP) depending on the isolated product. If aldehydes or ketones are the desired products, the reaction is viewed as the Oppenauer Oxidation.

Non-enolizable ketones with a relatively low reduction potential, such as benzophenone, can serve as the carbonyl component used as the hydride acceptor in this oxidation.

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Recent Literature

Oppenauer Oxidation of Secondary Alcohols with 1,1,1-Trifluoroacetone as Hydride Acceptor
R. Mello, J. Martínze-Ferrer, G. Asensio, M. E. González-Núñez, J. Org. Chem., 2007, 72, 9376-9378.

Efficient and Selective Al-Catalyzed Alcohol Oxidation via Oppenauer Chemistry
C. R. Graves, B.-S. Zeng, S. T. Nguyen, J. Am. Chem. Soc., 2006, 128, 12596-12597.

Practical Oppenauer (OPP) Oxidation of Alcohols with a Modified Aluminium Catalyst
T. Ooi, H. Otshuka, T. Miura, H. Ichikawa, K. Maruoka, Org. Lett., 2002, 4, 2669-2672.