Structures of Copper Complexes of the Hybrid [SNS] Ligand of Bis(2-(benzylthio)ethyl)amine and Facile Catalytic Formation of 1-Benzyl-4-phenyl-1H-1,2,3-triazole through Click Reaction

2009 ◽  
Vol 48 (3) ◽  
pp. 1207-1213 ◽  
Author(s):  
Shi-Qiang Bai ◽  
Lip Lin Koh ◽  
T. S. Andy Hor
Keyword(s):  
Copper Complexes ◽  
Click Reaction ◽  
Sns Ligand ◽  
Ethyl Amine

First example of a click-reaction on the aminate copper complexes: effect of reaction parameters

2018 ◽  
Vol 28 (6) ◽  
pp. 606-608 ◽  
Author(s):  
Igor V. Esarev ◽  
Vladislav V. Gurzhiy ◽  
Artem A. Selyutin ◽  
Anastasia V. Laptenkova ◽  
Andrey I. Poddel'sky ◽  
...  
Keyword(s):  
Copper Complexes ◽  
Click Reaction ◽  
Reaction Parameters

scholarly journals Copper(II) Complexes of N-Propargyl Cyclam Ligands Reveal a Range of Coordination Modes and Colours, and Unexpected Reactivity

2020 ◽  
Author(s):  
Andrew Counsell ◽  
Mingfeng Yu ◽  
Mengying Shi ◽  
Angus Jones ◽  
James M. Batten ◽  
...  
Keyword(s):  
Coordination Chemistry ◽  
Copper Complexes ◽  
Click Reaction ◽  
Copper Binding ◽  
X Ray Diffraction ◽  
Enol Ether ◽  
X Ray ◽  
Coordination Modes ◽  
Triazole Ligand ◽  
Binding Behaviour

<p>Herein we describe single crystal X-ray diffraction and spectroscopic investigations of the coordination chemistry of copper(II) complexes of cyclam derivatives with between 1 and 4 pendant alkynes. The crystal structures of these copper complexes unexpectedly reveal a range of coordination modes, and the surprising occurrence of five unique complexes within a single recrystallisation of the tetra-<i>N</i>-propargyl cyclam ligand. One of these species exhibits weak intramolecular copper-alkyne coordination, and another is formed by a surprising intramolecular copper-mediated hydroalkoxylation reaction with the solvent methanol, transforming one of the pendant alkynes to an enol ether. Multiple functionalisation of the tetra-<i>N</i>-propargyl ligand is demonstrated <i>via</i> a ‘tetra-click’ reaction with benzyl azide, and the copper-binding behaviour of the resulting tetra-triazole ligand is characterised spectroscopically.</p>

New organometallic Schiff-base copper complexes as efficient “click” reaction precatalysts

2016 ◽  
Vol 40 (4) ◽  
pp. 3308-3313 ◽  
Author(s):  
Xiang Liu ◽  
Néstor Novoa ◽  
Carolina Manzur ◽  
David Carrillo ◽  
Jean-René Hamon
Keyword(s):  
Schiff Base ◽  
High Activity ◽  
Copper Complexes ◽  
Click Reaction ◽  
Sodium Ascorbate

In the presence of sodium ascorbate, recyclable CuAAC precatalysts displayed high activity allowing the synthesis of a wide variety of 1,4-disubstituted 1,2,3-triazoles in high isolated yields.

scholarly journals Isolation of bis(copper) key intermediates in Cu-catalyzed azide-alkyne “click reaction”

2015 ◽  
Vol 1 (5) ◽  
pp. e1500304 ◽  
Author(s):  
Liqun Jin ◽  
Daniel R. Tolentino ◽  
Mohand Melaimi ◽  
Guy Bertrand
Keyword(s):  
Direct Observation ◽  
Copper Complexes ◽  
Click Reaction ◽  
Life Sciences ◽  
Dipolar Cycloaddition ◽  
Dinuclear Complexes ◽  
Chemical Transformations ◽  
Terminal Alkyne ◽  
Mechanistic Studies ◽  
Copper Acetylide

The copper-catalyzed 1,3-dipolar cycloaddition of an azide to a terminal alkyne (CuAAC) is one of the most popular chemical transformations, with applications ranging from material to life sciences. However, despite many mechanistic studies, direct observation of key components of the catalytic cycle is still missing. Initially, mononuclear species were thought to be the active catalysts, but later on, dinuclear complexes came to the front. We report the isolation of both a previously postulated π,σ-bis(copper) acetylide and a hitherto never-mentioned bis(metallated) triazole complex. We also demonstrate that although mono- and bis-copper complexes promote the CuAAC reaction, the dinuclear species are involved in the kinetically favored pathway.

scholarly journals Copper(II) Complexes of N-Propargyl Cyclam Ligands Reveal a Range of Coordination Modes and Colours, and Unexpected Reactivity

2020 ◽  
Author(s):  
Andrew Counsell ◽  
Mingfeng Yu ◽  
Mengying Shi ◽  
Angus Jones ◽  
James M. Batten ◽  
...  
Keyword(s):  
Coordination Chemistry ◽  
Copper Complexes ◽  
Click Reaction ◽  
Copper Binding ◽  
X Ray Diffraction ◽  
Enol Ether ◽  
X Ray ◽  
Coordination Modes ◽  
Triazole Ligand ◽  
Binding Behaviour

<p>Herein we describe single crystal X-ray diffraction and spectroscopic investigations of the coordination chemistry of copper(II) complexes of cyclam derivatives with between 1 and 4 pendant alkynes. The crystal structures of these copper complexes unexpectedly reveal a range of coordination modes, and the surprising occurrence of five unique complexes within a single recrystallisation of the tetra-<i>N</i>-propargyl cyclam ligand. One of these species exhibits weak intramolecular copper-alkyne coordination, and another is formed by a surprising intramolecular copper-mediated hydroalkoxylation reaction with the solvent methanol, transforming one of the pendant alkynes to an enol ether. Multiple functionalisation of the tetra-<i>N</i>-propargyl ligand is demonstrated <i>via</i> a ‘tetra-click’ reaction with benzyl azide, and the copper-binding behaviour of the resulting tetra-triazole ligand is characterised spectroscopically.</p>

scholarly journals Crystal structure of [bis(2-aminoethyl-κN)(2-{[4-(trifluoromethyl)benzylidene]amino}ethyl)amine-κN]dichloridocopper(II)

2016 ◽  
Vol 72 (1) ◽  
pp. 83-86
Author(s):  
Katherine A. Bussey ◽  
Annie R. Cavalier ◽  
Margaret E. Mraz ◽  
Ashley S. Holderread ◽  
Kayode D. Oshin ◽  
...  
Keyword(s):  
Copper Complexes ◽  
Coordination Geometry ◽  
Asymmetric Unit ◽  
Aromatic Rings ◽  
Bond Lengths ◽  
Pyramidal Geometry ◽  
Jahn Teller ◽  
Square Pyramidal Geometry ◽  
Ethyl Amine ◽  
Van Der Waals Contacts

The CuIIatom in the title compound, [CuCl2(C14H21F3N4)], adopts a coordination geometry that is between distorted square-based pyramidal and very Jahn–Teller-elongated octahedral. It is coordinated by three N atoms from the bis(2-aminoethyl)(2-{[4-(trifluoromethyl)benzylidene]amino}ethyl)amine and two chloride ligands. The two crystallographically unique copper complexes present in the asymmetric unit exhibit noticeable differences in the coordination bond lengths. Considering the CuIIatoms as having square-pyramidal geometry, the basal Cu—Cl bond lengths are typical [2.2701 (12) and 2.2777 (12) Å], while the apical distances are considerably elongated [2.8505 (12) and 2.9415 (12) Å]. For each molecule, a CuIIatom from inversion-related molecules are in nearby proximity to the remaining axial CuIIsites, but the Cu...Cl distances are very long [3.4056 (12) and 3.1645 (12) Å], attributable to van der Waals contacts. Nonetheless, these contacts appear to have some structure-directing properties, leading to association into dimers. These dimers associateviastacking of the aromatic rings to form extended zigzag chains.

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