Room Temperature Copper(II)-Catalyzed Oxidative Cyclization of Enamides to 2,5-Disubstituted Oxazoles via Vinylic C–H Functionalization

Author(s)
Cheung, Chi Wai; Buchwald, Stephen Leffler
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Abstract
A copper(II)-catalyzed oxidative cyclization of enamides to oxazoles via vinylic C–H bond functionalization at room temperature is described. Various 2,5-disubstituted oxazoles bearing aryl, vinyl, alkyl, and heteroaryl substituents could be synthesized in moderate to high yields. This reaction protocol is complementary to our previously reported iodine-mediated cyclization of enamides to afford 2,4,5-trisubstituted oxazoles.
Date issued
2012-07
URI
http://hdl.handle.net/1721.1/81976
Department
Massachusetts Institute of Technology. Department of Chemistry
Journal
The Journal of Organic Chemistry
Publisher
American Chemical Society (ACS)
Citation
Cheung, Chi Wai, and Stephen L. Buchwald. “Room Temperature Copper(II)-Catalyzed Oxidative Cyclization of Enamides to 2,5-Disubstituted Oxazoles via Vinylic C–H Functionalization.” The Journal of Organic Chemistry 77, no. 17 (September 7, 2012): 7526-7537.
Version: Author's final manuscript
ISSN
0022-3263
1520-6904
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