Facile Rh(III)-Catalyzed Synthesis of Fluorinated Pyridines

Org Lett. 2015 Jun 5;17(11):2567-9. doi: 10.1021/acs.orglett.5b00979. Epub 2015 May 20.

Abstract

A Rh(III)-catalyzed C-H functionalization approach was developed for the preparation of multisubstituted 3-fluoropyridines from α-fluoro-α,β-unsaturated oximes and alkynes. Oximes substituted with aryl, heteroaryl, and alkyl β-substituents were effective coupling partners, as were symmetrical and unsymmetrical alkynes with aryl and alkyl substituents. The first examples of coupling α,β-unsaturated oximes with terminal alkynes was also demonstrated and proceeded with uniformly high regioselectivity to provide single 3-fluoropyridine regioisomers. Reactions were also conveniently set up in air on the benchtop.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Catalysis
  • Halogenation
  • Hydrocarbons, Fluorinated / chemical synthesis*
  • Hydrocarbons, Fluorinated / chemistry
  • Molecular Structure
  • Organoselenium Compounds / chemistry*
  • Pyridines / chemistry*
  • Rhodium / chemistry*

Substances

  • Hydrocarbons, Fluorinated
  • Organoselenium Compounds
  • Pyridines
  • Rhodium