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Copper(II)-benzotriazole coordination compounds in click chemistry: a diagnostic reactivity study
journal contribution
posted on 2023-06-09, 13:06 authored by Edouardos Loukopoulos, Alaa Abdul-Sada, Gizella Csire, Csilla Kállay, Adam Brookfield, Graham J Tizzard, Simon J Coles, Ioannis N Lykakis, George KostakisGeorge KostakisThis diagnostic study aims to shed light on the catalytic activity of a library of Cu(II) based coordination compounds with benzotriazole-based ligands. We report herein the synthesis and characterization of five new coordination compounds formulated [CuII(L4)(MeCN)2(CF3SO3)2] (1), [CuII(L5)2(CF3SO3)2] (2), [CuII(L6)2(MeCN)(CF3SO3)]·(CF3SO3) (3), [CuII(L6)2(H2O)(CF3SO3)]·(CF3SO3)·2(Me2CO) (4), [CuI4(L1)2(L1’)2(CF3SO3)2]2·4(CF3SO3)·8(Me2CO) (5), derived from similar nitrogen-based ligands. The homogeneous catalytic activity of these compounds along with our previously reported coordination compounds (6 -13), derived from similar ligands, is tested against the well-known Cu(I)-catalysed azide-alkyne cycloaddition reaction. The optimal catalyst [CuII(L1)2(CF3SO3)2] (10) activates the reaction to afford 1,4-disubstituted 1,2,3-triazoles with yields up to 98% and without requiring a reducing agent. Various control experiments are performed to optimize the method as well as examine parameters such as ligand variation, metal coordination geometry and environment, in order to elucidate the behaviour of the catalytic system.
History
Publication status
- Published
File Version
- Accepted version
Journal
Dalton TransactionsISSN
1477-9226Publisher
Royal Society of ChemistryExternal DOI
Issue
31Volume
47Page range
10491-10508Department affiliated with
- Chemistry Publications
Full text available
- Yes
Peer reviewed?
- Yes
Legacy Posted Date
2018-04-30First Open Access (FOA) Date
2019-05-01First Compliant Deposit (FCD) Date
2018-04-30Usage metrics
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