New electrophilic difluoromethylating reagent

Org Lett. 2007 May 10;9(10):1863-6. doi: 10.1021/ol070195g. Epub 2007 Apr 20.

Abstract

A new electrophilic difluoromethylating reagent has been developed. The S-(difluoromethyl)diarylsulfonium tetrafluoroborate has been shown to be effective for the introduction of an electrophilic difluoromethyl group into the following nucleophiles: sulfonic acids, tertiary amines, imidazole derivatives, and phosphines. The reagent failed to transfer the difluoromethyl group to phenols, carbon nucleophiles, and primary and secondary amines.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemistry
  • Boric Acids / chemistry
  • Electrons*
  • Fluorine / chemistry*
  • Imidazoles / chemistry
  • Indicators and Reagents / chemistry
  • Methylation
  • Molecular Structure
  • Nitroimidazoles / chemistry
  • Phosphines / chemistry
  • Sulfones / chemistry
  • Sulfonium Compounds / chemical synthesis
  • Sulfonium Compounds / chemistry

Substances

  • Amines
  • Boric Acids
  • Imidazoles
  • Indicators and Reagents
  • Nitroimidazoles
  • Phosphines
  • Sulfones
  • Sulfonium Compounds
  • sulfonidazole
  • Fluorine
  • phosphine
  • boric acid