Suzuki−Miyaura Coupling of NHC−Boranes: A New Addition to the C−C Coupling Toolbox

Suzuki−Miyaura Coupling of NHC−Boranes: A New Addition to the C−C Coupling Toolbox

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 Csp2−Csp2 and Csp2−Csp3 carbon−carbon bond formation with trifla...

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Bibliographic Details
Published in:Organic letters Vol. 11; no. 21; pp. 4914 - 4917
Main Authors: Monot, Julien, Brahmi, Malika Makhlouf, Ueng, Shau-Hua, Robert, Carine, Murr, Marine Desage-El, Curran, Dennis P, Malacria, Max, Fensterbank, Louis, Lacôte, Emmanuel
Format: Journal Article
Language:English
Published: United States American Chemical Society 05-11-2009
Online Access:Get full text
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Summary: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 Csp2−Csp2 and Csp2−Csp3 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.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol902012c