Organic Letters 2009-11-05

Suzuki-Miyaura coupling of NHC-boranes: a new addition to the C-C coupling toolbox.

Julien Monot, Malika Makhlouf Brahmi, Shau-Hua Ueng, Carine Robert, Marine Desage-El Murr, Dennis P Curran, Max Malacria, Louis Fensterbank, Emmanuel Lacôte

Index: Org. Lett. 11 , 4914, (2009)

Full Text: HTML

Abstract

Complexes of triaryl- and trialkylboranes with N-heterocyclic carbenes (NHCs) participate in Suzuki-Miyaura cross-coupling reactions and provide coupled products in good yields under base-free conditions. The reaction can be applied to Csp(2)-Csp(2) and Csp(2)-Csp(3) carbon-carbon bond formation with triflates, iodides, bromides, and chlorides. These results enrich the utility of NHC-borane complexes, which can be added to the toolkit of Suzuki-Miyaura cross-couplings, along with boronic acids and organotrifluoroborates.