Aminodifluorosulfinium tetrafluoroborate salts as stable and crystalline deoxofluorinating reagents

Org Lett. 2009 Nov 5;11(21):5050-3. doi: 10.1021/ol902039q.

Abstract

Aminodifluorosulfinium tetrafluoroborate salts were found to act as efficient deoxofluorinating reagents when promoted by an exogenous fluoride source and, in most cases, exhibited greater selectivity by providing less elimination byproduct as compared to DAST and Deoxo-Fluor. Aminodifluorosulfinium tetrafluoroborates are easy handled crystalline salts that show enhanced thermal stability over dialkylaminosulfur trifluorides, are storage-stable, and unlike DAST and Deoxo-Fluor do not react violently with water.

MeSH terms

  • Borates / chemistry*
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Hydrocarbons, Fluorinated / chemical synthesis*
  • Hydrocarbons, Fluorinated / chemistry
  • Indicators and Reagents
  • Molecular Structure
  • Salts
  • Sulfinic Acids / chemistry*
  • Water / chemistry

Substances

  • Borates
  • Hydrocarbons, Fluorinated
  • Indicators and Reagents
  • Salts
  • Sulfinic Acids
  • Water