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

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.

• Authors: Rhia M Martin, Robert G Bergman, Jonathan A Ellman
• Journal: The Journal of organic chemistry (J Org Chem) Vol. 77 Issue 5 Pg. 2501-7 (Mar 02 2012) ISSN: 1520-6904 [Electronic] United States
• PMID: 22332639 (Publication Type: Journal Article, Research Support, N.I.H., Extramural, Research Support, Non-U.S. Gov't, Research Support, U.S. Gov't, Non-P.H.S.)

Chemical References

• Alkynes
• Oximes
• Pyridines
• Rhodium

Topics

• Alkynes (chemistry)
• Catalysis
• Molecular Structure
• Oximes (chemistry)
• Pyridines (chemical synthesis, chemistry)
• Rhodium (chemistry)
• Stereoisomerism