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
Externally publishedYes

Fingerprint

Fluorination
Pyrroles
Fluorides
Organic compounds
Electrolytes
Salts
Fluorine
Electrons
Derivatives
N-methylpyrrole

Keywords

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

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Analytical Chemistry
  • Electrochemistry

Cite this

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title = "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",
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.",
keywords = "2-Acetyl-1-methylpyrrole, 2-Cyano-1-methylpyrrole, 2-Formyl-1 -methylpyrrole, Anodic fluorination, Oxidation potential",
author = "Toshiki Tajima and Hideki Ishii and Toshio Fuchigami",
year = "2001",
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pages = "467--471",
journal = "Electrochemistry Communications",
issn = "1388-2481",
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TY - JOUR

T1 - Electrolytic partial fluorination of organic compounds. Part 51. Electrochemical fluorination of 1-methylpyrroles having electron-withdrawing groups at the 2-position

T2 - Effect of supporting fluoride salts on the fluorinated product selectivity

AU - Tajima, Toshiki

AU - Ishii, Hideki

AU - Fuchigami, Toshio

PY - 2001

Y1 - 2001

N2 - 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.

AB - 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.

KW - 2-Acetyl-1-methylpyrrole

KW - 2-Cyano-1-methylpyrrole

KW - 2-Formyl-1 -methylpyrrole

KW - Anodic fluorination

KW - Oxidation potential

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DO - 10.1016/S1388-2481(01)00185-0

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JF - Electrochemistry Communications

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