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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 26, Number 4
BKCSDE 26(4)
April 20, 2005 

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*
Aromatic fluorination, Triazine, Ionic liquid, Balz-Schiemann reaction
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 oC 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.
599 - 602
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