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Heterogeneous azide–alkyne cycloaddition in the presence of a copper catalyst supported on an ionic liquid polymer/silica hybrid material
Author(s) -
Fehér Klaudia,
Nagy Enikő,
Szabó Péter,
Juzsakova Tatjána,
Srankó Dávid,
Gömöry Ágnes,
Kollár László,
SkodaFöldes Rita
Publication year - 2018
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.4343
Subject(s) - chemistry , copper , ferrocene , catalysis , raman spectroscopy , azide , alkyne , hybrid material , heterogeneous catalysis , polymer chemistry , ionic liquid , benzil , cycloaddition , inorganic chemistry , organic chemistry , physics , electrode , optics , electrochemistry
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.