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http://dx.doi.org/10.5012/bkcs.2010.31.9.2571

Effects of Ion and Protic Solvent on Nucleophilic Aromatic Substitution (SNAr) Reactions  

Park, Sung-Woo (Department of Applied Chemistry, Kyung Hee University)
Lee, Sung-Yul (Department of Applied Chemistry, Kyung Hee University)
Publication Information
Bulletin of the Korean Chemical Society / v.31, no.9, 2010 , pp. 2571-2574 More about this Journal
Abstract
We investigate the mechanism of $S_NAr$ fluorination reactions under the influence of protic solvents and ions. We find that counterion or protic solvent alone retards the $S_NAr$ reactions, but together they may promote the reaction. In this mechanism, the protic solvent acts on the counterion as a Lewis base, and the nucleophile reacts as an ion pair. We also show that an anion (mesylate) may exhibit catalytic effects, suggesting the role of ionic liquids for accelerating the $S_NAr$ reactions.
Keywords
Ion; Protic solvents; SNAr;
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