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Org Biomol Chem. 2007 Feb 21;5(4):671-8. Epub 2007 Jan 12.

Efficient Heck reactions catalyzed by a highly recyclable palladium(II) complex of a pyridyl-functionalized imidazolium-based ionic liquid.

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Department of Chemistry, University of Idaho, Moscow, Idaho 83844-2343, USA.


The reactions of 2-(2-pyridyl)imidazole with alkyl iodides at 25 degrees C in the presence of base gave rise to 1-alkyl-2-(2-pyridyl)imidazole. Subsequent neat reactions with alkyl or polyfluoroalkyl halides at 100 degrees C, followed by anion exchange with LiN(SO(2)CF(3))(2), generated the mono-quaternary ionic liquids. All of them have excellent thermal stability and wide liquid range. Most of the salts with asymmetric N-substituents are liquid at room temperature. The effect of N-substituent variation and symmetry on NMR, TGA and DSC is discussed. Reaction of with palladium(II) chloride produced a mononuclear palladium ionic liquid complex, the structure of which was confirmed by single-crystal X-ray diffraction analysis. The Heck cross-coupling reactions using in ionic liquid demonstrated excellent stability and recyclability.

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