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DOI: 10.1055/s-0028-1083459
Cu(II)-Mediated Cyclopropylation of Amides and Azoles
Contributor(s):Paul Knochel, Andrei GavryushinInstitut de Chimie des Substances Naturelles, Gif-sur-Yvette, France
Copper-Mediated N-Cyclopropylation of Azoles, Amides, and Sulfonamides by Cyclopropylboronic Acid
J. Org. Chem. 2008, 73: 6441-6444
Publication History
Publication Date:
23 October 2008 (online)
Key words
N-cyclopropylation - azaheterocycles - copper catalysis
Significance
The development of methods for attaching an N-cyclopropyl unit in a molecule is of great importance for current medicinal chemistry. Herein, a simple, convenient and quite versatile method for cyclopropanation of various azoles as well as amides and sulfonamides is described. It uses readily available inexpensive reagents and does not require special precautions like inert atmosphere. The process should be easy to scale up and therefore may find useful applications in industry.
Comment
An elegant Cu-promoted cyclopropanation of azoles with tricyclopropylbismuth was reported recently (A. Gagnon, M. St-Onge, K. Little, M. Duplessis, F. Barabé J. Am. Chem. Soc. 2007, 129, 44); however, cyclopropylboronic acid is better available as it is a commercial product.
Review
For a review on C-heteroatom bond formation via boronic acids, see: D. M. Chan, P. Y. S. Lam, In Boronic Acids: Preparation and Application in Organic Synthesis and Medicine, D. G. Hall, Ed.; Wiley-VCH: Weinheim, 2005, 204-240.