Enamide Synthesis by Copper-Catalyzed Cross-Coupling of Amides and Potassium Alkenyltrifluoroborate Salts†
Yuri Bolshan
Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON, M5S 3H6, Canada, Fax: (+1) 416-978-5059 http://www.chem.utoronto.ca/staff/RAB/index.html
Search for more papers by this authorRobert A. Batey Prof.
Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON, M5S 3H6, Canada, Fax: (+1) 416-978-5059 http://www.chem.utoronto.ca/staff/RAB/index.html
Search for more papers by this authorYuri Bolshan
Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON, M5S 3H6, Canada, Fax: (+1) 416-978-5059 http://www.chem.utoronto.ca/staff/RAB/index.html
Search for more papers by this authorRobert A. Batey Prof.
Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON, M5S 3H6, Canada, Fax: (+1) 416-978-5059 http://www.chem.utoronto.ca/staff/RAB/index.html
Search for more papers by this authorThe 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.
Graphical Abstract
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.
Supporting Information
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