Cu-Catalyzed amidation of vinyl halides: A highly efficient synthesis of a wide variety of heterocycles

ORGN 295

Ruben Martin, maparusa@mit.edu and Stephen L Buchwald. Department of Chemistry, Massachusetts Institute of Technology, 77, Massachusetts Ave, Cambridge, MA 02139
Metal-catalyzed C-N bond formations represent a crucial contribution to the synthetic methodologies for the preparation of nitrogen-containing compounds. While Cu-catalyzed C-N bond formations of aryl halides are a usual tool for cross-coupling reactions, it was only recently that extension of this chemistry to vinyl halides as substrates have been possible. Thus, an efficient copper-catalyzed coupling of readily accessible vinyl halides and primary amides is described herein. The resulting enamido-type products have shown to be very useful intermediates in the synthesis of highly substituted nitrogen-containing heterocyclic compounds, such as oxazoles, pyrroles and indole derivatives.