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

Loukopoulos, Edward, Abdul-Sada, Alaa, Csire, Gizella, Kállay, Csilla, Brookfield, Adam, Tizzard, Graham J, Coles, Simon J, Lykakis, Ioannis N and Kostakis, George E (2018) Copper(II)-benzotriazole coordination compounds in click chemistry: a diagnostic reactivity study. Dalton Transactions, 47 (31). pp. 10491-10508. ISSN 1477-9226

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Abstract

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.

Item Type: Article
Schools and Departments: School of Life Sciences > Chemistry
Subjects: Q Science > QD Chemistry > QD0146 Inorganic chemistry
Depositing User: Georgios Kostakis
Date Deposited: 30 Apr 2018 15:38
Last Modified: 01 Jul 2019 12:45
URI: http://sro.sussex.ac.uk/id/eprint/75541

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