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

Copper(II)-benzotriazole coordination compounds in click chemistry: a diagnostic reactivity study
Copper(II)-benzotriazole coordination compounds in click chemistry: a diagnostic reactivity study
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.
0300-9246
1-18
Loukopoulos, Edward
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Abdul-Sada, Alaa
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Csire, Gizella
e57552d7-e7d7-4183-bdf1-9260dc3dfcb7
Kállay, Csilla
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Brookfield, Adam
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Tizzard, Graham J.
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Coles, Simon J.
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Lykakis, Ioannis N.
911d7593-96d3-4de5-ab47-9af2586cdcb7
Kostakis, George E.
dd72c724-c82e-4891-aa68-ccdb42cc6cb8
Loukopoulos, Edward
0c3abad3-9ed4-46cd-b03f-9cbb2fd3fff7
Abdul-Sada, Alaa
03b55c32-8062-4b73-926d-f243ca078a83
Csire, Gizella
e57552d7-e7d7-4183-bdf1-9260dc3dfcb7
Kállay, Csilla
79186333-d507-48be-bed3-212c58b2e1fd
Brookfield, Adam
2ffd4e08-b79f-4324-bb37-52c1072f773a
Tizzard, Graham J.
8474c0fa-40df-43a6-a662-7f3c4722dbf2
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Lykakis, Ioannis N.
911d7593-96d3-4de5-ab47-9af2586cdcb7
Kostakis, George E.
dd72c724-c82e-4891-aa68-ccdb42cc6cb8

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, 1-18. (doi:10.1039/C8DT01256C).

Record type: Article

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.

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Accepted/In Press date: 30 April 2018
e-pub ahead of print date: 1 May 2018

Identifiers

Local EPrints ID: 422187
URI: https://eprints.soton.ac.uk/id/eprint/422187
ISSN: 0300-9246
PURE UUID: 904e1d99-2681-4d06-8b1f-589e0d9f5d33
ORCID for Graham J. Tizzard: ORCID iD orcid.org/0000-0002-1577-5779
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272

Catalogue record

Date deposited: 18 Jul 2018 16:30
Last modified: 06 Oct 2018 00:37

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