Two new copper(II) complexes with chelating N,O-type bidentate ligands: Synthesis, characterization, crystal structure and catalytic activity in azide–alkyne cycloaddition reaction

Bagherzadeh, Mojtaba; Bayrami, Arshad; Kia, Reza; Amini, Mojtaba; Cook, Laurence J. Kershaw; Raithby, Paul R.

doi:10.1016/j.ica.2017.06.046

Cited by 35 publications

(16 citation statements)

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“…Supported Cu(II) species have turned out to be very active after reduction using ascorbate (entries 7–11). The two Cu(II) complexes in entries 1 and 2, [57] which are active in AAC without pre‐treatment with a reductant, remain thus exclusive examples.…”

Section: Resultsmentioning

confidence: 99%

“…[86] Supported Cu(II) species have turned out to be very active after reduction using ascorbate (entries 7-11). The two Cu(II) complexes in entries 1 and 2, [57] which are active in AAC without pre-treatment with a reductant, remain thus exclusive examples. When compared to other Cu(I) based homogeneous catalysts (Table 3, entries 12-25), we can state that complex 1 is very suitable from several points of view.…”

Section: Catalytic Activity Of [Cu(pnp Ntph -Ph)cl] (1)mentioning

confidence: 99%

“…[56] The most common protocols thus use Cu(II) precursors such as CuSO 4 and a reducing agent such as sodium ascorbate. [53,54,57] The reaction of organic halides or aryl boronic acids with NaN 3 [58][59][60][61] leads to the pharmacologically important 1,2,3triazole heterocycles. [64][65][66][67] In this work, we describe the synthesis of the new Cu…”

Section: Introductionmentioning

confidence: 99%

“…Cu(I) can oxidised or disproportionate to Cu(II) or Cu(0) and Cu(II), respectively [56] . The most common protocols thus use Cu(II) precursors such as CuSO 4 and a reducing agent such as sodium ascorbate [53,54,57] . The reaction of organic halides or aryl boronic acids with NaN 3 [58–61] leads to the pharmacologically important 1,2,3‐triazole heterocycles [64–67] …”

Section: Introductionmentioning

confidence: 99%

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Redox Instability of Copper(II) Complexes of a Triazine‐Based PNP Pincer

et al. 2021

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The new Cu(I) complex [Cu(PNP NTPh-Ph)Cl] (1) containing the tridentate PNP pincer ligand N,N'-bis(diphenylphosphino)-2,6diamino-4-phenyl-1,3,5-triazine was obtained from the reaction of [Cu(SMe 2)Cl] n with the ligand as ether solvate 1. 0.5Et 2 O. 1 was independently obtained from a reaction mixture containing the ligand and the Cu(II) precursor CuCl 2. 2H 2 O in 50 % yield alongside with the Cu(II) coordination polymer [Cu(O 2 PPh 2) 2 ] n (2). From the reaction of Cu(NO 3) 2 • 3H 2 O with PNP NTPh-Ph in the presence of pyridine the complexes [Cu(O 2 PPh 2) 2 (Py) 2 (H 2 O)] (3), [Cu(O 2 PPh 2)(Py) 2 (NO 3)] 2 (4), and [Cu(Py) 4 (NO 3) 2 ]. Py (5), were obtained, 2, 3, and 4 contain diphenyl-phosphinate ligands. The underlying redox reaction of the ligand and Cu(II) yielding the oxidised ligands observed in the by-products and the Cu(I) product complex was further studied using electrochemistry and UV-vis spectroelectrochemistry. Attempts to synthesise the Cu(II) complex [Cu(PNP NTPh-Ph)(NO 3) 2 ] (6) in a mechanochemical experiment gave evidence for this unprecedented species from ESI-MS(+) and EPR spectroscopy but also revealed its very high sensitivity to air and moisture. The catalytic activity of 1 was investigated in the azide-alkyne cycloaddition yielding various 1-benzyl-4-phenyl-1H-1,2,3-triazoles. The environmentally benign ("green") and cheap EtOH/H 2 O solvent mixture turned out to be very suitable. Melting points, FT-IR, and NMR spectra of the triazole products were analysed.

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Section: Resultsmentioning

confidence: 99%

Section: Catalytic Activity Of [Cu(pnp Ntph -Ph)cl] (1)mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Redox Instability of Copper(II) Complexes of a Triazine‐Based PNP Pincer

et al. 2021

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“…20 There are many catalytic systems reported in the literature for the synthesis of 1,2,3-triazole derivatives via alkyne-azide 1,3dipolar cycloaddition reaction. [21][22][23][24][25][26][27][28][29][30][31] Each of the catalysts used in these reactions has its advantages and disadvantages. For example, copper(I) salts are very sensitive and will be oxidized to copper(II) compounds when exposed to air.…”

Section: Introductionmentioning

confidence: 99%

Immobilized copper nanoparticles on nitrogen-rich porous activated carbon from egg white biomass: a robust hydrophilic–hydrophobic balance catalyst for click reaction

et al. 2018

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Part‐per‐million catalysis of azide‐alkyne cycloaddition reaction in water using a new ferromagnetic μ_1,1‐N₃ bridged dinuclear Cu(II) complex

Mirdarvatan

Bahramian

Khalaji

et al. 2022

Applied Organom Chemis

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An original copper(II) dimeric compound formulated as [Cu2(μ1,1‐N3)2L2(N3)2].2CHCl3 (1), with L = 2,6‐pyridinedicarboxaldehydebis(p‐iodophenyl‐imine), has been synthesized and characterized. Single crystal X‐ray structural characterization revealed that this complex displays a centrosymmetric dinuclear structure in which the two Cu(II) centers are connected by double symmetric μ1,1 (end‐on, EO) azido bridges, generating distorted octahedral CuN6 coordination geometry. Magnetic susceptibility measurements indicate a ferromagnetic Cu···Cu coupling with J = 26.7 cm−1 (J being the parameter of the exchange Hamiltonian H = −2JS1S2). The catalytic properties of complex 1 have been evaluated in the one‐pot azide‐alkyne cycloaddition reaction in water without any additional reducing agents or bases. As expected, the absence of any catalyst did not lead to product formation, whereas when complex 1 was introduced as catalyst, the reaction led to the desired product with different chemical yields (10–98%), for which the highest one (98%) corresponds to the reaction performed in the presence of 125 ppm of 1 in water at 90 C. These optimized parameters have been then taken into account to extend the initial reaction based on benzyl chloride and simple alkyne to different substituted benzyl chloride and alkyne molecules.

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Two new copper(II) complexes with chelating N,O-type bidentate ligands: Synthesis, characterization, crystal structure and catalytic activity in azide–alkyne cycloaddition reaction

Cited by 35 publications

References 45 publications

Redox Instability of Copper(II) Complexes of a Triazine‐Based PNP Pincer

Redox Instability of Copper(II) Complexes of a Triazine‐Based PNP Pincer

Immobilized copper nanoparticles on nitrogen-rich porous activated carbon from egg white biomass: a robust hydrophilic–hydrophobic balance catalyst for click reaction

Part‐per‐million catalysis of azide‐alkyne cycloaddition reaction in water using a new ferromagnetic μ_1,1‐N₃ bridged dinuclear Cu(II) complex

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Two new copper(II) complexes with chelating N,O-type bidentate ligands: Synthesis, characterization, crystal structure and catalytic activity in azide–alkyne cycloaddition reaction

Cited by 35 publications

References 45 publications

Redox Instability of Copper(II) Complexes of a Triazine‐Based PNP Pincer

Redox Instability of Copper(II) Complexes of a Triazine‐Based PNP Pincer

Immobilized copper nanoparticles on nitrogen-rich porous activated carbon from egg white biomass: a robust hydrophilic–hydrophobic balance catalyst for click reaction

Part‐per‐million catalysis of azide‐alkyne cycloaddition reaction in water using a new ferromagnetic μ1,1‐N3 bridged dinuclear Cu(II) complex

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Part‐per‐million catalysis of azide‐alkyne cycloaddition reaction in water using a new ferromagnetic μ_1,1‐N₃ bridged dinuclear Cu(II) complex