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Synfacts 2009(1): 0096-0096  
DOI: 10.1055/s-0028-1087419
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Biomimetic Aldehyde Oxidation Catalyzed by NHCs

Contributor(s): Benjamin List, Steffen Müller
J. Guin, S. De Sarkar, S. Grimme, A. Studer*
Westfälische Wilhelms-Universität, Münster, Germany
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Publikationsverlauf

Publikationsdatum:
18. Dezember 2008 (online)

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Significance

The authors report a protocol for the organocatalytic oxidation of various aldehydes to the corresponding carboxylic acid derivatives. The reaction is catalyzed by simple N-heterocyclic carbenes (NHC) at low catalyst loadings (usually 0.5-2 mol%) and uses TEMPO as the stoichiometric oxidant. The procedure turned out to be highly efficient (yields up to 98%) and chemoselective with respect to several oxidizable functional groups.

Review: D. Enders, O. Niemeier, A. Henseler Chem. Rev. 2007, 107, 5606-5656.