Intermediacy of an N-heterocyclic carbene complex in the catalytic C-H activation of a substituted benzimidazole.
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.
Tan
Kian L
KL
Center for New Directions in Synthesis, Department of Chemistry, University of California-Berkeley, Berkeley, CA 94720, USA.
Bergman
Robert G
RG
Ellman
Jonathan A
JA
D001562:Benzimidazoles / Q000737:chemistry*; D002384:Catalysis; D006838:Hydrocarbons; D007700:Kinetics; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry*; D013816:Thermodynamics
D001562:Benzimidazoles; D006838:Hydrocarbons; C030011:carbene; D008697:Methane