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Regiospecific Synthesis of N-Alkyl-benzimidazoles from o-Haloanilines
N. Zheng, S. L. Buchwald*
Massachusetts Institute of Technology, Cambridge, USA
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.