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An Alternative Method for the Synthesis of N -Pentafluorophenyl Triazolium Salts.

Steven M LangdonMichel Gravel
Published in: Organic letters (2022)
A route for the synthesis of 1,2,4-triazolium salts via oxidation of a thione precursor is demonstrated. N -Pentafluorophenyl-substituted salts are produced in 20-63% overall yields. Isolation and purification of the azolium salts are simplified compared to the traditional synthetic route. Late-stage selection of the counterion allows the synthesis of a variety of salts from a parent thione. The salts have been compared in Stetter and cross-benzoin reactions with an appreciable counterion effect in both reactions.
Keyphrases
  • ionic liquid
  • hydrogen peroxide
  • molecular docking