Abstract
Triazolium-based ionic liquids are prepared in a straightforward two-step procedure. In the first step azides and alkynes are transformed into 1, 4-disubstituted 1,2,3-triazoles by Cu- mediated click-reaction. Subsequent alkylation affords 1,3,4-trisubstituted 1,2,3-triazolium salts as ionic liquids, which can be further modified by exchanging the anion by salt metathesis. The synthesis provides access to simple ionic liquids as well as to functionalized ionic liquids, bearing organocatalytic, fluorescent or linking groups thus representing task specific ionic liquids or IL-tagged organocatalysts, respectively.
Highlights
Ionic liquids (IL) are organic salts, which are liquid at temperatures below 100 °C
We report here full experimental data for the synthesis of 1,2,3-triazolium-based IL 5 and their precursors 4, the application of alternative versions of the triazole synthesis by using 20 mol% of Cu(II) in the presence of sodium ascorbate as well as the exchange of the anions X- in 5 by a salt metathesis reaction
Either acetonitrile or dichloromethane was used as solvent (Method C, D) or the reaction was implemented without an additional solvent using excess of alkylating reagent 4 (Method E)
Summary
Ionic liquids (IL) are organic salts, which are liquid at temperatures below 100 °C. They have a very low vapor pressure, high boiling points and their polarity can be varied in wide range depending on the nature of both anions and cations.[1,2] they can be used as preferable solvents in a number of cases. The resulting 1,2,3-triazolium salts 5 were isolated in quantitative yields by removing all volatile products under vacuum. We found a straightforward and very versatile access to trisubstituted 1,2,3triazolium salts 5 as a novel class of IL by a two-step procedure consisting of Cu-mediated cycloaddition reaction of azides 1 with alkynes 2 and alkylation of the resulting 1,2,3-triazoles 3.
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