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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 31, Number 9
BKCSDE 31(9)
September 20, 2010 

Effects of Ion and Protic Solvent on Nucleophilic Aromatic Substitution (SNAr) Reactions
Sungwoo Park, Sungyul Lee*
Ion, Protic solvents, SNAr
We investigate the mechanism of SNAr fluorination reactions under the influence of protic solvents and ions. We find that counterion or protic solvent alone retards the SNAr 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 SNAr reactions.
2571 - 2574
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