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Activation of Nucleophilic Fluorination by Salts in Ionic Liquids and in Sulfolane
Author(s) -
Anguille Stéphane,
Garayt Maxime,
Schanen Vincent,
Grée René
Publication year - 2006
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200606086
Subject(s) - sulfolane , chemistry , ionic liquid , bromide , nucleophile , nucleophilic substitution , solvent , organic chemistry , medicinal chemistry , substitution reaction , nucleophilic addition , ionic bonding , inorganic chemistry , ion , catalysis
The nucleophilic substitution of PhCCl 3 by KF in imidazolium‐type RTILs is faster than in classical organic solvents but it is strongly dependent upon the nature of the counteranion. The addition of bromide salts in substoichoimetric amounts to the [bmim][PF 6 ] solvent strongly accelerates this reaction. Furthermore, it has been discovered that addition of KPF 6 to the reaction mixtures strongly activates the nucleophilic fluorination by KF, not only in the [bmim][NTf 2 ] or [bmim][PF 6 ] ionic liquids but also for the reactions performed in sulfolane.
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