Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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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)
  • Received : 2010.05.10
  • Accepted : 2010.07.26
  • Published : 2010.09.20
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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.

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