Highly selective electrochemical fluorination of organic compounds in ionic liquids

Toshio Fuchigami, Toshiki Tajima

Research output: Contribution to journalArticle

37 Citations (Scopus)

Abstract

Recent studies on electrochemical partial fluorination in ionic liquid fluoride salts are reviewed. At first, historical background and some problems of electrochemical fluorination in organic solvents are briefly mentioned. Solvent-free electrochemical fluorinations in ionic liquids are explained as follows. Ultrasonication was found to improve both the yield and current efficiency for electrochemical fluorination of α-phenylthioacetate, which is mainly attributable to marked mass transport promotion of the substrate and the suppression of anode passivation. Highly regioselective and efficient fluorination of cyclic ethers, lactones, and cyclic carbonate was achieved in Et4NF·4HF and Et3N·5HF. Selective fluorination of hardly oxidizable phthalide was realized using a combination of imidazolium and fluoride ionic liquids. The unique effect of imidazolium ionic liquids on electrochemical fluorodesulfurization of 3-phenylthiophthalide was explained. Reuse of ionic liquids for electrochemical fluorination is also possible.

Original languageEnglish
Pages (from-to)181-187
Number of pages7
JournalJournal of Fluorine Chemistry
Volume126
Issue number2
DOIs
Publication statusPublished - 2005 Feb

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Keywords

  • Anodic fluorination
  • Fluorodesulfurization
  • Ionic liquid
  • Ultrasonication

ASJC Scopus subject areas

  • Biochemistry
  • Environmental Chemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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