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Chemistry of 1,2,3-Triazolium Salts

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Chemistry of 1,2,3-triazoles

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 40))

Abstract

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 1,2,3-triazolium 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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Abbreviations

Ar:

Aryl

Bn:

Benzyl

Boc:

Tert-butoxycarbonyl

cat:

Catalyst

Cbz:

Benzyloxycarbonyl

CuAAC:

Copper catalysed azide-alkyne cycloaddition

d:

Day(s)

DABCO:

1,4-diazabicyclo[2.2.2]octane

DCC:

N N-dicyclohexylcarbodiimide

DMAP:

4-(N N-dimethylamino)pyridine

DMF:

N N-dimethylformamide

DMSO:

Dimethyl sulphoxide

dr:

Diastereomer ratio

ee:

Enantiomer excess

equiv:

Equivalent(s)

Et:

Ethyl

Fmoc:

9-Fluorenylmethoxycarbonyl

h:

Hour(s)

IL(s):

Ionic liquids

iPr:

Isopropyl

KHMDS:

Potassium hexamethyldisilazide potassium bis(trimethylsilyl)amide

LDA:

Lithium diisopropylamide

Me:

Methyl

min:

Minute(s)

mol:

Mole(s)

nBu:

n-butyl

Nu:

Nucleophile

Ph:

Phenyl

Pr:

Propyl

py:

Pyridine

rt:

Room temperature

RTILs:

Room temperature ionic liquids

s:

Second(s)

TBAF:

Tetrabutylammonium fluoride

TBDMS:

Tert-butyldimethylsilyl

Tf:

Trifluoromethanesulphonyl (triflyl)

TFA:

Trifluoroacetic acid

THF:

Tetrahydrofuran

TIPS:

Triisopropylsilyl

TMEDA:

N,N,N′,N′-t etramethyl- 1,2-ethylenediamine

TMS:

Trimethylsilyl

Ts:

Tosyl (Tosyl) 4-toluenesulphonyl

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Authors and Affiliations

  1. Humboldt University of Berlin, Berlin, Germany

    Zekarias Yacob & Jürgen Liebscher

  2. National Institute for Research and Development of Isotopic and Molecular Technologies, 65-103 Donath, 400293, Cluj-Napoca, Romania

    Zekarias Yacob & Jürgen Liebscher

Authors
  1. Zekarias Yacob
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  2. Jürgen Liebscher
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Editors and Affiliations

  1. Department of Chemistry, KU Leuven, Leuven, Belgium

    Wim Dehaen

  2. Ural Federal University, Yekaterinburg, Russia

    Vasiliy A. Bakulev

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Yacob, Z., Liebscher, J. (2014). Chemistry of 1,2,3-Triazolium Salts. In: Dehaen, W., Bakulev, V. (eds) Chemistry of 1,2,3-triazoles. Topics in Heterocyclic Chemistry, vol 40. Springer, Cham. https://doi.org/10.1007/7081_2014_123

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