Synfacts 2007(3): 0307-0307  
DOI: 10.1055/s-2007-968178
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Amidation of Allylic and Benzylic C-H Bonds

Contributor(s): Paul Knochel, Andrei Gavryushin
G. Pelletier, D. A. Powell*
Merck Frosst Centre for Therapeutic Research, Kirkland, Canada
Further Information

Publication History

Publication Date:
20 February 2007 (online)

Significance

A direct regioselective formation of a C-N bond from a C-H bond is a synthetically extremely useful process, considering the great number of biologically active nitrogen-containing molecules. This is the first highly versatile amidation method which allows an easy preparation of both primary and secondary amides from corresponding alkanes. The amide and the oxidant are used directly, without the pre-synthesis of unstable intermediates. The reaction is quite simple to conduct, no protection from air or moisture is needed. It tolerates a broad number of functional groups, including simple amides.