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Issue 10, 2007
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Halide-free highly-pure imidazolium triflate ionic liquids: Preparation and use in palladium-catalysed allylic alkylation

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Abstract

The reaction of three oxygenated heterocycles (tetrahydrofuran, tetrahydropyran, 1,4-dioxane) with trifluoromethane sulfonic anhydride in the presence of the non-nucleophilic base poly(4-vinylpyridine) affords alkylditriflates quantitatively via ring opening. The alkylditriflates react with N-alkylimidazoles providing the bis-imidazolium bis-triflate salts in high yields. Hydroxymethyl substituted oxygenated heterocycles are converted into imidazolium triflate salts without opening of the heterocycle. Two imidazolium salts were characterized by X-ray crystallographic structure determination. The halide free ionic liquids were applied successfully as solvents in the palladium catalysed allylic alkylation. A co-crystal of 15 and tetrabutylammonium triflate has also been characterized by X-ray crystallographic structure analysis.

Graphical abstract: Halide-free highly-pure imidazolium triflate ionic liquids: Preparation and use in palladium-catalysed allylic alkylation

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Publication details

The article was received on 28 Feb 2007, accepted on 24 May 2007 and first published on 13 Jun 2007


Article type: Paper
DOI: 10.1039/B703096G
Citation: Green Chem., 2007,9, 1097-1103
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    Halide-free highly-pure imidazolium triflate ionic liquids: Preparation and use in palladium-catalysed allylic alkylation

    L. Leclercq, I. Suisse, G. Nowogrocki and F. Agbossou-Niedercorn, Green Chem., 2007, 9, 1097
    DOI: 10.1039/B703096G

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