Collect. Czech. Chem. Commun. 2007, 72, 417-434

Ionic Liquid Supports Stable Under Conditions of Peptide Couplings, Deprotections and Traceless Suzuki Reactions

Zoia Mincheva, Fabien Bonnette and Olivier Lavastre*

Institut de chimie, UMR 6226 CNRS - Université de Rennes 1, Campus de Beaulieu, 35042 Rennes Cedex, France


Ionic liquid supports (ILS) functionalized with carboxylic, alcoholic or amino groups were synthesized, based on 1-methylimidazolium and pyridinium cations, and bromide, chloride, iodide and tetrafluoroborate anions. These reactive ionic liquids were fully characterized by NMR and HRMS. Ionic liquids based on 1-(6-aminohexyl)-3-methylimidazolium iodide have been used in the conditions of peptide chemistry such as coupling and deprotection reactions. A method for attaching (bromophenyl)silanes to the ionic liquid supports was also developed to introduce traceless linkers. An ionic liquid with attached bromobenzene was reacted with ArB(OH)2 under the Suzuki cross-coupling conditions and the resulting compound was cleaved by bromodesilylation with Br2/pyridine to give the substituted products in good yields. The substrate loading of the ILS is high and can be tuned to between 2.5 and 5.0 mmol/g.

Keywords: Ionic liquid supports; Ionic liquids; Methylimidazolium salts; Peptide coupling; Traceless linkers; Suzuki cross-coupling.

References: 60 live references.