Reactivity of a hypervalent iodine trifluoromethylating reagent toward THF: ring opening and formation of trifluoromethyl ethers

J Org Chem. 2010 Mar 5;75(5):1779-82. doi: 10.1021/jo9025429.

Abstract

1-Trifluoromethyl-1,2-benziodoxol-3-(1H)-one (1) is able to transfer the electrophilic CF(3) group to the oxygen atom of THF in the presence of a Lewis or Bronsted acid. This results in a new ring-opening reaction of THF yielding trifluoromethyl ethers. Details of this reaction and the insight gained into the mechanism of action of reagent 1 are reported.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cyclization
  • Ethers / chemical synthesis*
  • Ethers / chemistry
  • Hydrocarbons, Fluorinated / chemical synthesis*
  • Hydrocarbons, Fluorinated / chemistry
  • Hydrocarbons, Halogenated / chemical synthesis
  • Hydrocarbons, Halogenated / chemistry*
  • Indicators and Reagents
  • Iodine / chemistry*
  • Magnetic Resonance Spectroscopy
  • Methylation
  • Molecular Structure
  • Structure-Activity Relationship

Substances

  • 1-trifluoromethyl-1,2-benziodoxol-3(1H)-one
  • Ethers
  • Hydrocarbons, Fluorinated
  • Hydrocarbons, Halogenated
  • Indicators and Reagents
  • Iodine