Electrolytic partial fluorination of organic compounds. Part 51. Electrochemical fluorination of 1-methylpyrroles having electron-withdrawing groups at the 2-position: Effect of supporting fluoride salts on the fluorinated product selectivity

Toshiki Tajima, Hideki Ishii, Toshio Fuchigami

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Anodic fluorination of 1-methylpyrroles having electron-withdrawing groups at the 2-position was comparatively studied using Et3N • 3HF and Et3N • 2HF as a supporting electrolyte and a fluorine source. The use of Et3N • 3HF gave trifluorinated products predominantly or selectively depending on solvents used while the use of Et3N • 2HF provided the corresponding monofluorinated pyrrole derivatives in considerable amount along with the trifluorinated products regardless of the solvents. This is the first successful example of selective anodic fluorination of pyrroles. The effects of supporting electrolyte on product selectivity are discussed.

Original languageEnglish
Pages (from-to)467-471
Number of pages5
JournalElectrochemistry Communications
Volume3
Issue number8
DOIs
Publication statusPublished - 2001 Aug 16

Keywords

  • 2-Acetyl-1-methylpyrrole
  • 2-Cyano-1-methylpyrrole
  • 2-Formyl-1 -methylpyrrole
  • Anodic fluorination
  • Oxidation potential

ASJC Scopus subject areas

  • Electrochemistry

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