4.7 Article

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

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 17, Pages 7526-7537

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo301332s

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Funding

  1. National Institutes of Health (NIH) [GM58160]
  2. Croucher Foundation (Hong Kong)

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A copper(11)-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.

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