Synthesis of pyridines from ketoximes and terminal alkynes via C-H bond functionalization

J Org Chem. 2012 Mar 2;77(5):2501-7. doi: 10.1021/jo202280e. Epub 2012 Feb 14.

Abstract

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 α,β-unsaturated ketoximes. The use of electron-deficient phosphite ligands is important to suppress dimerization of the terminal alkynes to enynes.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alkynes / chemistry*
  • Catalysis
  • Molecular Structure
  • Oximes / chemistry*
  • Pyridines / chemical synthesis*
  • Pyridines / chemistry
  • Rhodium / chemistry
  • Stereoisomerism

Substances

  • Alkynes
  • Oximes
  • Pyridines
  • Rhodium