A new strategy for the synthesis of poly-substituted 3-H, 3-fluoro, or 3-trifluoromethyl pyridines via the tandem C-F bond cleavage protocol

Org Lett. 2010 Oct 1;12(19):4376-9. doi: 10.1021/ol101859p.

Abstract

A new strategy for the synthesis of poly-substituted 3-H, 3-F, and 3-trifluoromethyl pyridines based on C-F bond breaking of the anionically activated fluoroalkyl group is described. A series of 2,6-disubstituted 4-amino pyridines were prepared through this domino process in high yields under noble metal-free conditions, making this method a supplement to pyridine synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbon / chemistry*
  • Crystallography, X-Ray
  • Cyclization
  • Fluorine / chemistry*
  • Fluorine Compounds / chemical synthesis*
  • Models, Molecular
  • Molecular Structure
  • Pyridines / chemical synthesis*

Substances

  • Fluorine Compounds
  • Pyridines
  • trifluoromethylpyridine
  • Fluorine
  • Carbon