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

Bulletin of the Korean chemical society

Dae Yoon Chi¹  Sung-Woo Park¹  Sung-Woo Jang¹  Choong Eui Song¹  Sungyul Lee¹  Byoung Se Lee¹ 

关键词: Mechanism;    SNAr;    Molten salt;   

DOI  :  

学科分类：化学（综合）

来源: Korean Chemical Society

【 摘 要 】

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).

【 授权许可】

Unknown