A free-radical cascade trifluoromethylation/cyclization of N-arylmethacrylamides and enynes with sodium trifluoromethanesulfinate and iodine pentoxide

Org Lett. 2014 Jul 18;16(14):3688-91. doi: 10.1021/ol5014747. Epub 2014 Jul 1.

Abstract

An I(2)O(5)-promoted free-radical cascade trifluoromethylation/cyclization of a broad range of N-arylmethacrylamides and enynes with sodium trifluoromethanesulfinate in aqueous medium has been achieved. This strategy allows highly selective access to a variety of CF(3)-containing oxindoles and pyrrolidines. Electron spin resonance (ESR) studies indicate that atom-transfer processes are involved in this system.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acrylamides / chemistry*
  • Alkynes / chemistry*
  • Catalysis
  • Cyclization
  • Electron Spin Resonance Spectroscopy
  • Free Radicals
  • Hydrocarbons, Fluorinated / chemical synthesis*
  • Hydrocarbons, Fluorinated / chemistry
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Iodine Compounds / chemistry*
  • Molecular Structure
  • Oxides / chemistry*
  • Oxindoles
  • Sodium / chemistry

Substances

  • Acrylamides
  • Alkynes
  • Free Radicals
  • Hydrocarbons, Fluorinated
  • Indoles
  • Iodine Compounds
  • Oxides
  • Oxindoles
  • 2-oxindole
  • Sodium
  • methacrylamide
  • iodine pentoxide