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NHC-Catalyzed Chemo- and Regioselective Hydrosilylation of Carbonyl Derivatives

Qiwu Zhao, Dennis P. Curran, Max Malacria, Louis Fensterbank*, Jean-Philippe Goddard*, Emmanuel Lacôte*

*UPMC Univ Paris 06, Institut Parisien de Chimie Moléculaire (UMR CNRS 7201), C. 229, 4 place Jussieu, 75005 Paris, France, Email: louis.fensterbankupmc.fr, jean-philippe.goddardupmc.fr, emmanuel.lacoteicsn.cnrs-gif.fr

Q. Zhao, D. P. Curran, M. Malacria, L. Fensterbank, J.-P. Goddard, E. Lacôte, Synlett, 2012, 23, 433-437.

DOI: 10.1055/s-0031-1290208 (free Supporting Information)


Abstract

Activation of diphenylsilane in the presence of a catalytic amount of an N-heterocyclic carbene (NHC) enables hydrosilylation of carbonyl derivatives under mild conditions. Presumably, a hypervalent silicon intermediate featuring strong Lewis acid character allows dual activation of both the carbonyl moiety and the hydride at the silicon center. Some interesting selectivities have been encountered.

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Key Words

hydrosilylation, reduction of carbonyl compouds, N-heterocyclic carbenes, diphenylsilane, organocatalysis, green chemistry


ID: J60-Y2012-0460