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 language | English (US) |
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Pages (from-to) | 599-602 |
Number of pages | 4 |
Journal | Bulletin of the Korean Chemical Society |
Volume | 26 |
Issue number | 4 |
DOIs | |
State | Published - Apr 20 2005 |
Keywords
- Aromatic fluorination
- Balz-Schiemann reaction
- Ionic liquid
- Triazine
ASJC Scopus subject areas
- General Chemistry