Jump to main content
Jump to site search

Issue 2, 2011
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Supplementary files

Publication details

The article was received on 15 Jul 2010, accepted on 16 Sep 2010 and first published on 15 Oct 2010


Article type: Paper
DOI: 10.1039/C0OB00426J
Citation: Org. Biomol. Chem., 2011,9, 418-422
  •   Request permissions

    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

Search articles by author

Spotlight

Advertisements