Issue 2, 2011

SN2 Fluorination reactions in ionic liquids: a mechanistic study towards solvent engineering

Abstract

In the catalysis of SN2 fluorination reactions, the ionic liquid anion plays a key role as a Lewis base by binding to the counterion Cs+ and thereby reducing the retarding Coulombic influence of Cs+ on the nucleophile F. The reaction rates also depend critically on the structures of ionic liquid cation, for example, n-butyl imidazolium gives no SN2 products, whereas n-butylmethyl imidazolium works well. The origin of the observed phenomenal synergetic effects by the ionic liquid [mim-tOH][OMs], in which t-butanol is bonded covalently to the cation [mim], is that the t-butanol moiety binds to the leaving group of the substrate, moderating the retarding interactions between the acidic hydrogen and F. This work is a significant step toward designing and engineering solvents for promoting specific chemical reactions.

Graphical abstract: SN2 Fluorination reactions in ionic liquids: a mechanistic study towards solvent engineering

Supplementary files

Article information

Article type
Paper
Submitted
15 Jul 2010
Accepted
16 Sep 2010
First published
15 Oct 2010

Org. Biomol. Chem., 2011,9, 418-422

SN2 Fluorination reactions in ionic liquids: a mechanistic study towards solvent engineering

Y. Oh, H. B. Jang, S. Im, M. J. Song, S. Kim, S. Park, D. Y. Chi, C. E. Song and S. Lee, Org. Biomol. Chem., 2011, 9, 418 DOI: 10.1039/C0OB00426J

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