PMID: 11916392Mar 28, 2002Paper

Intermediacy of an N-heterocyclic carbene complex in the catalytic C-H activation of a substituted benzimidazole

Journal of the American Chemical Society
K L TanJonathan A Ellman

Abstract

An N-heterocyclic carbene complex was found to be the active catalyst in the Rh(I)-catalyzed intramolecular coupling of an alkenyl group to a C-H bond of a substituted benzimidazole. Kinetic studies demonstrated that the catalytic cyclization is zero-order in substrate and first-order in catalyst. Furthermore, DFT calculations with a model system suggest that the rate-limiting step involves insertion of the alkenyl double bond into the rhodium-carbene bond.

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