4.7 Article

Synthesis of Pyridines from Ketoximes and Terminal Alkynes via C-H Bond Functionalization

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 5, Pages 2501-2507

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo202280e

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Funding

  1. NIH [GM069559]
  2. Office of Energy Research, Office of Basic Energy Science, Chemical Sciences Division, U.S. Department of Energy [DE-AC02-05CH11231]
  3. National Science Foundation
  4. University of California, Berkeley

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An expedient one-pot rhodium catalyzed C-H bond functionalization/electrocyclization/dehydration procedure has been developed for the synthesis of highly substituted pyridine derivatives from terminal alkynes and alpha,beta-unsaturated ketoximes. The use of electron-deficient phosphite ligands is important to suppress dimerization of the terminal alkynes to enynes.

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