An unexpected reaction of trimethylsilyl fluorosulfonyldifluoroacetate (TFDA) with imidazoles. Formation of N-difluoromethylthioureas

Org Lett. 2006 Nov 23;8(24):5549-51. doi: 10.1021/ol062213k.

Abstract

A new reaction of the efficient difluorocarbene-generating reagent trimethylsilyl fluorosulfonyldifluoroacetate (TFDA) is reported in which molecules containing an N-alkylimidazole or benzimidazole structure undergo an unexpected one-pot conversion to N-difluoromethylthioureas. [reaction: see text].

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Adenine / chemistry
  • Benzimidazoles / chemical synthesis
  • Catalysis
  • Imidazoles / chemistry*
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Spectrophotometry, Ultraviolet
  • Sulfur / chemistry
  • Thiourea / analogs & derivatives*
  • Thiourea / chemical synthesis*
  • Trimethylsilyl Compounds / chemistry*

Substances

  • Benzimidazoles
  • Imidazoles
  • Indicators and Reagents
  • Trimethylsilyl Compounds
  • trimethylsilyl fluorosulfonyldifluoroacetate
  • Sulfur
  • Thiourea
  • Adenine