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

Edward Loukopoulos, Alaa Abdul-Sada, Gizella Csire, C. Kállay, Adam Brookfield, Graham J. Tizzard, Simon J. Coles, Ioannis N. Lykakis, George E. Kostakis

Research output: Contribution to journalArticle

2 Citations (Scopus)

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 as [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), and [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 and examine parameters such as ligand variation, metal coordination geometry and environment, in order to elucidate the behaviour of the catalytic system.

Original languageEnglish
Pages (from-to)10491-10508
Number of pages18
JournalDalton Transactions
Volume47
Issue number31
DOIs
Publication statusPublished - Jan 1 2018

Fingerprint

Copper
Ligands
Catalyst activity
Triazoles
Alkynes
Azides
Cycloaddition
Reducing Agents
Nitrogen
Metals
Catalysts
Geometry
benzotriazole
Experiments

ASJC Scopus subject areas

  • Inorganic Chemistry

Cite this

Loukopoulos, E., Abdul-Sada, A., Csire, G., Kállay, C., Brookfield, A., Tizzard, G. J., ... Kostakis, G. E. (2018). Copper(II)-benzotriazole coordination compounds in click chemistry: a diagnostic reactivity study. Dalton Transactions, 47(31), 10491-10508. https://doi.org/10.1039/c8dt01256c

Copper(II)-benzotriazole coordination compounds in click chemistry : a diagnostic reactivity study. / Loukopoulos, Edward; Abdul-Sada, Alaa; Csire, Gizella; Kállay, C.; Brookfield, Adam; Tizzard, Graham J.; Coles, Simon J.; Lykakis, Ioannis N.; Kostakis, George E.

In: Dalton Transactions, Vol. 47, No. 31, 01.01.2018, p. 10491-10508.

Research output: Contribution to journalArticle

Loukopoulos, E, Abdul-Sada, A, Csire, G, Kállay, C, Brookfield, A, Tizzard, GJ, Coles, SJ, Lykakis, IN & Kostakis, GE 2018, 'Copper(II)-benzotriazole coordination compounds in click chemistry: a diagnostic reactivity study', Dalton Transactions, vol. 47, no. 31, pp. 10491-10508. https://doi.org/10.1039/c8dt01256c
Loukopoulos, Edward ; Abdul-Sada, Alaa ; Csire, Gizella ; Kállay, C. ; Brookfield, Adam ; Tizzard, Graham J. ; Coles, Simon J. ; Lykakis, Ioannis N. ; Kostakis, George E. / Copper(II)-benzotriazole coordination compounds in click chemistry : a diagnostic reactivity study. In: Dalton Transactions. 2018 ; Vol. 47, No. 31. pp. 10491-10508.
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