Synfacts 2008(2): 0190-0190  
DOI: 10.1055/s-2007-992478
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Regiospecific Synthesis of N-Alkyl-benzimidazoles from o-Haloanilines

Contributor(s): Paul Knochel, Andrei Gavryushin
N. Zheng, S. L. Buchwald*
Massachusetts Institute of Technology, Cambridge, USA
Further Information

Publication History

Publication Date:
23 January 2008 (online)


Benzimidazoles find a broad range of applications in material science, as well as biologically active compounds. They are sometimes difficult to prepare in regioisomerically pure form. This method uses available 2-haloanilines and primary amides as starting materials. It is a combination of the Cu(I)-catalyzed amidation with the subsequent ring closure, affording products with complete regioselectivity. This method is more economical and substantially less sensitive to the substitution pattern than similar Pd-catalyzed processes.