Preparation and synthetic applications of aryl tetraflates (ArOSO2CF2CF2H)

J Org Chem. 2008 Jan 18;73(2):711-4. doi: 10.1021/jo701630a. Epub 2007 Dec 18.

Abstract

We have recently developed an improved synthetic route to 1,1,2,2-tetrafluoroethanesulfonic acid (HCF2CF2SO3H, TFESA) and explored the applications of this newly available superacid in catalysis. Low volatility, ease of handling, and a convenient 1H NMR handle make this acid an attractive alternative to triflic acid. TFESA can also be converted to several of its derivatives: anhydride, sulfonyl chloride, and sulfonyl fluoride, which provide a good entry point for the synthesis of aryl sulfonates. We prepared several aryl esters of 1,1,2,2-tetrafluoroethanesulfonic acid (aryl tetraflates) and showed that they can be used in a number of palladium-catalyzed coupling reactions (Suzuki, Heck, and Buchwald-Hartwig couplings). While the reactivity of tetraflates lies between that of triflates and chlorides, tetraflates appear to be more thermally stable. Additionally, the presence of a hydrogen atom in the tetraflate group facilitates monitoring of reactions and characterization of derivatives.

MeSH terms

  • Arylsulfonates / chemical synthesis*
  • Arylsulfonates / chemistry
  • Catalysis
  • Hydrocarbons, Fluorinated / chemistry*
  • Magnetic Resonance Spectroscopy / methods
  • Molecular Structure
  • Stereoisomerism
  • Sulfonic Acids / chemistry*

Substances

  • 1,1,2,2-tetrafluoroethanesulfonic acid
  • Arylsulfonates
  • Hydrocarbons, Fluorinated
  • Sulfonic Acids