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http://dx.doi.org/10.5012/bkcs.2005.26.4.599

Aromatic Fluorination by Decomposition of Triazenes in Ionic Liquids  

Chu, Chan-Kook (Department of Chemistry, Inha University)
Kim, Jong-Hwan (Department of Chemistry, Inha University)
Kim, Dong-Wook (Department of Chemistry, Inha University)
Chung, Kyoo-Hyun (Department of Chemistry, Inha University)
Katzenellenbogen, John A. (Department of Chemistry, University of Illinois)
Chi, Dae-Yoon (Department of Chemistry, Inha University)
Publication Information
Bulletin of the Korean Chemical Society / v.26, no.4, 2005 , pp. 599-602 More about this Journal
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][$BF_4$], 2.5 mL) proceeds very smoothly at 80 ${^{\circ}C}$ 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.
Keywords
Aromatic fluorination; Triazine; Ionic liquid; Balz-Schiemann reaction;
Citations & Related Records
Times Cited By KSCI : 2  (Citation Analysis)
Times Cited By Web Of Science : 11  (Related Records In Web of Science)
Times Cited By SCOPUS : 11
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