Heterogeneous azide-alkyne cycloaddition in the presence of a copper catalyst supported on an ionic liquid polymer/silica hybrid material

Klaudia Fehér, Eniko a. Nagy, Péter Szabó, Tatjána Juzsakova, Dávid Srankó, A. Gömöry, L. Kollár, R. Skoda-Földes

Research output: Contribution to journalArticle

Abstract

Heterogeneous copper catalysts were prepared by the deposition of CuI on a hybrid material consisting of silica and a polymer with imidazolium moieties. The solid materials were characterised using solid-phase NMR, Fourier transform infrared, Raman and X-ray photoelectron spectroscopies and Brunauer-Emmett-Teller measurements. The formation of copper-carbene complexes was proved from Raman spectra and the results were supported by density functional theory calculations. The catalyst could be recycled efficiently with low loss of copper. Metal leaching was proved to be facilitated by the use of conditions typical for a homogeneous system (the presence of a polar solvent or the addition of a tertiary amine). Besides simple model reactions, the best catalyst was found to be suitable for the synthesis of triazoles of more elaborate structure, such as ferrocene or steroid derivatives.

Original languageEnglish
JournalApplied Organometallic Chemistry
DOIs
Publication statusAccepted/In press - Jan 1 2018

Fingerprint

Ionic Liquids
Alkynes
Azides
Cycloaddition
Hybrid materials
Catalyst supports
Silicon Dioxide
Copper
Polymers
Catalysts
Triazoles
Leaching
Amines
Density functional theory
Raman scattering
Fourier transforms
X ray photoelectron spectroscopy
Metals
Steroids
Nuclear magnetic resonance

Keywords

  • CuAAC reaction
  • DFT calculations
  • Raman spectroscopy
  • Recyclability
  • Triazole

ASJC Scopus subject areas

  • Chemistry(all)
  • Inorganic Chemistry

Cite this

Heterogeneous azide-alkyne cycloaddition in the presence of a copper catalyst supported on an ionic liquid polymer/silica hybrid material. / Fehér, Klaudia; Nagy, Eniko a.; Szabó, Péter; Juzsakova, Tatjána; Srankó, Dávid; Gömöry, A.; Kollár, L.; Skoda-Földes, R.

In: Applied Organometallic Chemistry, 01.01.2018.

Research output: Contribution to journalArticle

@article{caf0ac59f7684e63a3da665d3ba908e1,
title = "Heterogeneous azide-alkyne cycloaddition in the presence of a copper catalyst supported on an ionic liquid polymer/silica hybrid material",
abstract = "Heterogeneous copper catalysts were prepared by the deposition of CuI on a hybrid material consisting of silica and a polymer with imidazolium moieties. The solid materials were characterised using solid-phase NMR, Fourier transform infrared, Raman and X-ray photoelectron spectroscopies and Brunauer-Emmett-Teller measurements. The formation of copper-carbene complexes was proved from Raman spectra and the results were supported by density functional theory calculations. The catalyst could be recycled efficiently with low loss of copper. Metal leaching was proved to be facilitated by the use of conditions typical for a homogeneous system (the presence of a polar solvent or the addition of a tertiary amine). Besides simple model reactions, the best catalyst was found to be suitable for the synthesis of triazoles of more elaborate structure, such as ferrocene or steroid derivatives.",
keywords = "CuAAC reaction, DFT calculations, Raman spectroscopy, Recyclability, Triazole",
author = "Klaudia Feh{\'e}r and Nagy, {Eniko a.} and P{\'e}ter Szab{\'o} and Tatj{\'a}na Juzsakova and D{\'a}vid Srank{\'o} and A. G{\"o}m{\"o}ry and L. Koll{\'a}r and R. Skoda-F{\"o}ldes",
year = "2018",
month = "1",
day = "1",
doi = "10.1002/aoc.4343",
language = "English",
journal = "Applied Organometallic Chemistry",
issn = "0268-2605",
publisher = "John Wiley and Sons Ltd",

}

TY - JOUR

T1 - Heterogeneous azide-alkyne cycloaddition in the presence of a copper catalyst supported on an ionic liquid polymer/silica hybrid material

AU - Fehér, Klaudia

AU - Nagy, Eniko a.

AU - Szabó, Péter

AU - Juzsakova, Tatjána

AU - Srankó, Dávid

AU - Gömöry, A.

AU - Kollár, L.

AU - Skoda-Földes, R.

PY - 2018/1/1

Y1 - 2018/1/1

N2 - Heterogeneous copper catalysts were prepared by the deposition of CuI on a hybrid material consisting of silica and a polymer with imidazolium moieties. The solid materials were characterised using solid-phase NMR, Fourier transform infrared, Raman and X-ray photoelectron spectroscopies and Brunauer-Emmett-Teller measurements. The formation of copper-carbene complexes was proved from Raman spectra and the results were supported by density functional theory calculations. The catalyst could be recycled efficiently with low loss of copper. Metal leaching was proved to be facilitated by the use of conditions typical for a homogeneous system (the presence of a polar solvent or the addition of a tertiary amine). Besides simple model reactions, the best catalyst was found to be suitable for the synthesis of triazoles of more elaborate structure, such as ferrocene or steroid derivatives.

AB - Heterogeneous copper catalysts were prepared by the deposition of CuI on a hybrid material consisting of silica and a polymer with imidazolium moieties. The solid materials were characterised using solid-phase NMR, Fourier transform infrared, Raman and X-ray photoelectron spectroscopies and Brunauer-Emmett-Teller measurements. The formation of copper-carbene complexes was proved from Raman spectra and the results were supported by density functional theory calculations. The catalyst could be recycled efficiently with low loss of copper. Metal leaching was proved to be facilitated by the use of conditions typical for a homogeneous system (the presence of a polar solvent or the addition of a tertiary amine). Besides simple model reactions, the best catalyst was found to be suitable for the synthesis of triazoles of more elaborate structure, such as ferrocene or steroid derivatives.

KW - CuAAC reaction

KW - DFT calculations

KW - Raman spectroscopy

KW - Recyclability

KW - Triazole

UR - http://www.scopus.com/inward/record.url?scp=85045837688&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85045837688&partnerID=8YFLogxK

U2 - 10.1002/aoc.4343

DO - 10.1002/aoc.4343

M3 - Article

JO - Applied Organometallic Chemistry

JF - Applied Organometallic Chemistry

SN - 0268-2605

ER -