An unexpected reaction of trimethylsilyl fluorosulfonyldifluoroacetate (TFDA) with imidazoles. Formation of N-difluoromethylthioureas.
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].
Xu
Wei
W
Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200, USA.
Abboud
Khalil A
KA
Ghiviriga
Ion
I
Dolbier
William R
WR
Rapp
Magdalena
M
Wnuk
Stanislaw F
SF
D000225:Adenine / Q000737:chemistry; D001562:Benzimidazoles / Q000138:chemical synthesis; D002384:Catalysis; D007093:Imidazoles / Q000737:chemistry*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013056:Spectrophotometry, Ultraviolet; D013455:Sulfur / Q000737:chemistry; D013890:Thiourea / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
D001562:Benzimidazoles; D007093:Imidazoles; D007202:Indicators and Reagents; D014297:Trimethylsilyl Compounds; C522751:trimethylsilyl fluorosulfonyldifluoroacetate; D013455:Sulfur; D013890:Thiourea; D000225:Adenine