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Copper(II)-benzotriazole coordination compounds in click chemistry: a diagnostic reactivity study

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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 Kostakis
This 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 Transactions

ISSN

1477-9226

Publisher

Royal Society of Chemistry

Issue

31

Volume

47

Page range

10491-10508

Department affiliated with

  • Chemistry Publications

Full text available

  • Yes

Peer reviewed?

  • Yes

Legacy Posted Date

2018-04-30

First Open Access (FOA) Date

2019-05-01

First Compliant Deposit (FCD) Date

2018-04-30

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