The Natural Science and Engineering Research Council (NSERC) of Canada funded this research. Y.B. thanks the NSERC for a postgraduate scholarship (PGS D3) and the Walter C. Sumner Memorial Fellowship for funding. We also thank Dr. Alex Young for mass spectrometry analysis and Dr. Tim Burrow for assistance with NMR spectroscopy.
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Communication
Enamide Synthesis by Copper-Catalyzed Cross-Coupling of Amides and Potassium Alkenyltrifluoroborate Salts†
Article first published online: 31 JAN 2008
DOI: 10.1002/anie.200704711
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Issue
Angewandte Chemie International Edition
Volume 47, Issue 11, pages 2109–2112, February 28, 2008
Additional Information
How to Cite
Bolshan, Y. and Batey, Robert A. (2008), Enamide Synthesis by Copper-Catalyzed Cross-Coupling of Amides and Potassium Alkenyltrifluoroborate Salts. Angew. Chem. Int. Ed., 47: 2109–2112. doi: 10.1002/anie.200704711
- †
Publication History
- Issue published online: 22 FEB 2008
- Article first published online: 31 JAN 2008
- Manuscript Received: 12 OCT 2007
Funded by
- Natural Science and Engineering Research Council (NSERC) of Canada
- NSERC
- Walter C. Sumner Memorial Fellowship
Keywords:
- copper;
- cross-coupling;
- enamides;
- homogeneous catalysis
A new partner: Potassium alkenyltrifluoroborate salts undergo coupling with amides to give enamides in the presence of a Cu(OAc)2 catalyst and under mild oxidative conditions (see scheme). The air- and water-stable alkenyltrifluoroborate salts offer a convenient alternative to alkenyl halides as cross-coupling partners. A range of amides undergo coupling including cyclic amides, imides, and carbamates as well as benzamides.