Copper(ii)-benzotriazole coordination compounds in click chemistry: a diagnostic reactivity study. Issue 31 (24th May 2018)

• Record Type: Journal Article
• Authors: Loukopoulos, Edward; Abdul-Sada, Alaa; Csire, Gizella; Kállay, Csilla; Brookfield, Adam; Tizzard, Graham J.; Coles, Simon J.; Lykakis, Ioannis N.; Kostakis, George E.
• Is Part Of: Dalton transactions. Volume 47:Issue 31(2018)
• Page Start: 10491
• Page End: 10508
• Publication Date: 2018-05-24
• Subjects: Chemistry, Inorganic -- Periodicals; Chemistry, Physical and theoretical -- Periodicals; Chemistry, Inorganic -- Periodicals; 546.05
• DOI: 10.1039/c8dt01256c
• Languages: English
• ISSNs: 1477-9226

Abstract

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. 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 [Cu II (L 4 )(MeCN)2 (CF3 SO3 )2 ] (1 ), [Cu II (L 5 )2 (CF3 SO3 )2 ] (2 ), [Cu II (L 6 )2 (MeCN)(CF3 SO3 )]·(CF3 SO3 ) (3 ), [Cu II (L 6 )2 (H2 O)(CF3 SO3 )]·(CF3 SO3 )·2(Me2 CO) (4 ), and [CuI4(L 1 )2 (L 1′ )2 (CF3 SO3 )2 ]2 ·4(CF3 SO3 )·8(Me2 CO) (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 [Cu II (L 1 )2 (CF3 SO3 )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.