Synfacts 2006(4): 0382-0382  
DOI: 10.1055/s-2006-934328
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

A Versatile Method for Suzuki Cross-Coupling of Nitrogen Heterocycles

Contributor(s): Paul Knochel, Andrei Gavryushin
N. Kudo, M. Perseghini, G. C. Fu*
Massachusetts Institute of Technology, Cambridge, USA
Further Information

Publication History

Publication Date:
24 March 2006 (online)

Significance

Despite the tremendous number of recently developed highly active catalysts for Suzuki cross-coupling reactions, a coupling reaction of nitrogen-containing heterocycles may sometimes be a significant challenge. In this publication, a general and robust protocol for the Suzuki cross-coupling of various types of aza-heterocycles is presented. The method uses inexpensive tricyclohexylphosphine as a ligand and a relatively low amount (1 mol%) of palladium catalyst. Even the often unreactive electron-rich aryl chlorides can be successfully involved in the cross-coupling reaction under these conditions.