Synthesis and application of azolium ionic liquid tagged TADDOL catalysts

Yacob, Zekarias; Liebscher, Jürgen

doi:10.3998/ark.5550190.0013.322

Cited by 5 publications

(1 citation statement)

References 23 publications

(30 reference statements)

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“…1 A logical extension of our previous studies on imidazolium-based systems was to examine 1,3-dialkyl-1,2,3-triazolium 2·X, which have been described as stable and recyclable solvents. [15][16][17][18] The present study is focused on the application of the AER (A¯ form) method for the iodide-to-anion exchange of the selected triazolium ion pairs. The reported synthesis of 1-benzyl-3-methyl-1,2,3-triazolium iodide 2b·I ([BnmTr]I) requires benzyl azide 4 for the preparation of the click-derived 1,2,3-triazole 3, 15 as shown in the retrosyntetic Scheme 1.…”

Section: Introductionmentioning

confidence: 99%

Azolium-based systems: application of an anion exchange resin (A- form) method and 1H NMR analysis of the charged-assisted (C–H)+•anion hydrogen bonds

Dinarés¹,

Mesquida²,

Ibáñez³

et al. 2013

Arkivoc

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Dedicated to Prof. Rosa M. Claramunt on the occasion of her 65th birthday AbstractThe counteranion exchange of quaternary 1,2,3-triazolium salts was examined using a simple method that permitted halide ions to be swap for a variety of anions using an anion exchange resin (A¯ form). The method was applied to 1,2,3-triazolium-based ionic liquids and the iodideto-anion exchange proceeded in excellent to quantitative yields, concomitantly removing halide impurities. Additionally, an anion exchange resin (N 3¯ form) was used to obtain the benzyl azide from benzyl halide under mild reaction. Likewise, following a similar protocol, bis(azidomethyl)arenes were also synthesized in excellent yields. The results of a proton NMR spectroscopic study of simple azolium-based ion pairs are discussed, with attention focused on the significance of the charged-assisted (C-H) + ···anion hydrogen bonds of simple azolium systems such as 1-butyl-3-methylimidazolium and 1-benzyl-3-methyl-1,2,3-triazolium salts.

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Section: Introductionmentioning

confidence: 99%

Azolium-based systems: application of an anion exchange resin (A- form) method and 1H NMR analysis of the charged-assisted (C–H)+•anion hydrogen bonds

Dinarés¹,

Mesquida²,

Ibáñez³

et al. 2013

Arkivoc

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Chemistry of 1,2,3-Triazolium Salts

Yacob¹,

Liebscher²

2014

Topics in Heterocyclic Chemistry

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1,2,3-Triazolium salts have been known for a long time. However, their potential as ionic liquids and catalysts was recognized only quite recently. 1,2,3-Triazolium ionic liquids can serve as solvent, as catalyst, as hosts in anion recognition and as components of molecular machines. The major trends in application involve tethering catalytically active species such as (S)-proline with triazolium ionic liquids and the use as anion recognizing organocatalysts. Such catalysts are interesting not only due to their recyclability but also because of their outstanding tuneable properties. They can have wide liquid range, thermal stability, tuneable polarity, low flammability, tuneable solubility and low vapour pressure along with ease of separation. The syntheses of 1,2,3-triazolium salts are mainly based on the copper catalysed azide-alkyne cycloaddition (CuAAC) as the most famous click reaction, and subsequent N-alkylation of the resulting 1,2,3-triazoles. This synthetic route has the advantage of having four structural units, i.e. the alkyne, the azide, the alkylating agent and the counter anion that can be manipulated in order to tune the properties of the resulting ionic liquid. Unlike the imidazolium ionic liquids 1,2,3-triazolium salts do not have an acidic proton at position 2, which could make them inappropriate for reactions under basic conditions. The low acidity of 1,2,3triazolium salts in position 4 is exploited in the formation of 1,2,3-triazol-4-ylidene metal complexes with marked catalytic properties.

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Five-Membered Ring Systems

Aitken

Power

2013

Progress in Heterocyclic Chemistry

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Synthesis and application of azolium ionic liquid tagged TADDOL catalysts

Cited by 5 publications

References 23 publications

Azolium-based systems: application of an anion exchange resin (A- form) method and 1H NMR analysis of the charged-assisted (C–H)+•anion hydrogen bonds

Azolium-based systems: application of an anion exchange resin (A- form) method and 1H NMR analysis of the charged-assisted (C–H)+•anion hydrogen bonds

Chemistry of 1,2,3-Triazolium Salts

Five-Membered Ring Systems

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