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http://dx.doi.org/10.5012/bkcs.2012.33.3.881

Very Efficient Nucleophilic Aromatic Fluorination Reaction in Molten Salts: A Mechanistic Study  

Jang, Sung-Woo (Department of Applied Chemistry, Kyunghee University)
Park, Sung-Woo (Department of Applied Chemistry, Kyunghee University)
Lee, Byoung-Se (Department of Chemistry, Sogang University)
Chi, Dae-Yoon (Department of Chemistry, Sogang University)
Song, Choong-Eui (Department of Chemistry and Department of Energy Science, Sungkyunkwan University)
Lee, Sung-Yul (Department of Applied Chemistry, Kyunghee University)
Publication Information
Bulletin of the Korean Chemical Society / v.33, no.3, 2012 , pp. 881-884 More about this Journal
Abstract
We report a quantum chemical study of an extremely efficient nucleophilic aromatic fluorination in molten salts. We describe that the mechanism involves solvent anion interacting with the ion pair nucleophile $M^+F^-$(M = Na, K, Rb, Cs) to accelerate the reaction. We show that our proposed mechanism may well explain the excellent efficiency of molten salts for SNAr reactions, the relative efficacy of the metal cations, and also the observed large difference in rate constants in two molten salts $(n-C_4H_9)_4N^+\;CX_3SO_3^-$, (X=H, F) with slightly different sidechain ($-CH_3$ vs. $-CF_3$).
Keywords
Mechanism; SNAr; Molten salt;
Citations & Related Records
Times Cited By KSCI : 2  (Citation Analysis)
Times Cited By Web Of Science : 1  (Related Records In Web of Science)
Times Cited By SCOPUS : 1
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