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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 33, Number 3
BKCSDE 33(3)
March 20, 2012

Title	Very Efficient Nucleophilic Aromatic Fluorination Reaction in Molten Salts: A Mechanistic Study
Author	Sung-Woo Jang, Sung-Woo Park, Byoung Se Lee, Dae Yoon Chi,* Choong Eui Song,* Sungyul Lee*
Keywords	Mechanism, SNAr, Molten salt
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-C4H9)4N+ CX3SO3 −, (X=H, F) with slightly different sidechain (-CH3 vs. -CF3).
Page	881 - 884
Full Text	PDF

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