Acid-mediated formation of trifluoromethyl sulfonates from sulfonic acids and a hypervalent iodine trifluoromethylating agent

Chem Commun (Camb). 2009 Oct 28:(40):5993-5. doi: 10.1039/b913962a. Epub 2009 Sep 14.

Abstract

A variety of sulfonic acids have been trifluoromethylated using 1-trifluoromethyl-1,2-benziodoxol-3(1H)-one under mild conditions in good to excellent yields. Initial mechanistic investigations of this reaction show a clean second-order kinetics and only very weak substrate electronic effects.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkanesulfonates / chemistry*
  • Allyl Compounds
  • Hydrocarbons, Halogenated / chemistry*
  • Iodine
  • Methylation
  • Molecular Structure
  • Sulfonic Acids / chemistry*

Substances

  • 1-trifluoromethyl-1,2-benziodoxol-3(1H)-one
  • Alkanesulfonates
  • Allyl Compounds
  • Hydrocarbons, Halogenated
  • Sulfonic Acids
  • Iodine