Aromatic fluorination by decomposition of triazenes in ionic liquids

Chan Kook Chu, Jong Hwan Kim, Dong Wook Kim, Kyoo Hyun Chung, John A. Katzenellenbogen, Dae Yoon Chi

Research output: Contribution to journalArticlepeer-review

Abstract

The aromatic fluorination method involving the acid-catalyzed decomposition of a triazene in an ionic liquid is a very convenient and efficient way to prepare a variety of aromatic fluorides in a lab-scale. It should be particularly useful for the preparation aryl fluorides substituted with electron withdrawing substituents. Fluorination of triazene 1 (1.0 mmol) and p-toluenesulfonic acid (1.2 mmol) in an ionic liquid, 1-butyl-3- methylimidazolium tetrafluoroborate ([bmim][BF4], 2.5 mL) proceeds very smoothly at 80°C with or without an external source of fluoride, providing 73% yield in 30 min. Unlike diazonium salts, triazene precursors are stable enough to be stored for a long period of time without a noticeable decomposition.

Original languageEnglish (US)
Pages (from-to)599-602
Number of pages4
JournalBulletin of the Korean Chemical Society
Volume26
Issue number4
DOIs
StatePublished - Apr 20 2005

Keywords

  • Aromatic fluorination
  • Balz-Schiemann reaction
  • Ionic liquid
  • Triazine

ASJC Scopus subject areas

  • General Chemistry

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