Thiophene-containing dinucleating ligands for the copper-catalyzed oxidative coupling of 2,6-dimethylphenol

Huisman, Mieke; Koval, Iryna A.; Gámez, Patrick; Reedijk, Jan

doi:10.1016/j.ica.2005.06.055

Cited by 14 publications

(15 citation statements)

References 20 publications

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“…Likewise, Reedijk and co-workers have also shown that a series of Cu II complexes incorporating structurally related N,O-containing ligands or dinucleating phenol-based ''end-off'' compartmental N,O,S-ligands underwent this polymerization more efficiently than copper(II) salts [43,44]. Consistent with our view, Hirao et al pointed out that the bidentate or multidentate coordination of flexible N-heterocyclic ligands was considered to be a key factor for the construction of efficient oxygenation systems [45]. Table 3 lists the best experimental results of the complexes investigated and the reported highly active catalysts for this process.…”

Section: Catalytic Properties Of Complexessupporting

confidence: 84%

Catalytic applications of CuII-containing MOFs based on N-heterocyclic ligand in the oxidative coupling of 2,6-dimethylphenol

Xiao

Hou

Fan

2007

Journal of Organometallic Chemistry

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Section: Catalytic Properties Of Complexessupporting

confidence: 84%

Catalytic applications of CuII-containing MOFs based on N-heterocyclic ligand in the oxidative coupling of 2,6-dimethylphenol

Xiao

Hou

Fan

2007

Journal of Organometallic Chemistry

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“…3-(Chloromethyl)-2-hydroxy-5-methylbenzaldehyde ( B ) was obtained from 5-methyl-2-hydroxybenzaldehyde ( A ) via a previously described chloromethylation reaction. 23,24 …”

Section: Experimental Sectionmentioning

confidence: 99%

Dicopper(II) and Dizinc(II) Complexes with Nonsymmetric Dinucleating Ligands Based on Indolo[3,2-c]quinolines: Synthesis, Structure, Cytotoxicity, and Intracellular Distribution

et al. 2013

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Dicopper(II) and dizinc(II) complexes [Cu2(MeOOCLCOO)(CH3COO)2] (1) and [Zn2(MeOOCLCOO)(CH3COO)2] (2) were synthesized by reaction of Cu(CH3COO)2·H2O and Zn(CH3COO)2·2H2O with a new nonsymmetric dinucleating ligand EtOOCHLCOOEt prepared by condensation of 6-hydrazinyl-11H-indolo[3,2-c]quinoline with diethyl-2,2′-((3-formyl-2-hydroxy-5-methylbenzyl)azanediyl)diacetate. The design and synthesis of this elaborate ligand was performed with the aim of increasing the aqueous solubility of indolo[3,2-c]quinolines, known as biologically active compounds, and investigating the antiproliferative activity in human cancer cell lines and the cellular distribution by exploring the intrinsic fluorescence of the indoloquinoline scaffold. The compounds have been comprehensively characterized by elemental analysis, spectroscopic methods (IR, UV–vis, 1H and 13C NMR spectroscopy), ESI mass spectrometry, magnetic susceptibility measurements, and UV–vis complex formation studies (for 1) as well as by X-ray crystallography (1 and 2). The antiproliferative activity of EtOOCHLCOOEt, 1, and 2 was determined by the MTT assay in three human cancer cell lines, namely, A549 (nonsmall cell lung carcinoma), CH1 (ovarian carcinoma), and SW480 (colon adenocarcinoma), yielding IC50 values in the micromolar concentration range and showing dependence on the cell line. The effect of metal coordination on cytotoxicity of EtOOCHLCOOEt is also discussed. The subcellular distribution of EtOOCHLCOOEt and 2 was investigated by fluorescence microscopy, revealing similar localization for both compounds in cytoplasmic structures.

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“…An alternative strategy was developed by using a weak thiophene donor group to model the thioether and prevent coordination to Cu II , as it occurs in type 3 copper proteins. [24][25][26] However, poor catecholase activity was reported for copper(II)c o m p l e x e s bearing a bis-thiophene ligand. Also the role of the thiophene groups in the catalytic reaction was not evoked.…”

Section: Introductionmentioning

confidence: 99%

Rate enhancement of the catechol oxidase activity of a series of biomimetic monocopper(ii) complexes by introduction of non-coordinating groups in N-tripodal ligands

et al. 2012

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Asymmetrical N-tripodal ligands have been synthesized in three steps. Diversity has been introduced at the first step of the synthesis by adding pyrazine, pyridine, benzyl and thiophene rings. The corresponding Cu II complexes have been prepared by reaction with CuCl 2 and characterized by Electron Paramagnetic Resonance (EPR), UV-Vis spectroscopies and cyclic voltammetry. The data show that the ligand coordinates to Cu II in a mononuclear fashion in solution and that the complexes display a square pyramidal geometry. All complexes are characterized by a quasi-reversible one-electron redox behavior in acetonitrile. The ability of the complexes to oxidize 3,5-di-tert-butylcatechol to 3,5-di-tert-butylquinone has been studied and the results show that the rate of the reaction depends on the basicity and the steric hindrance of the heterocyclic donor. Best results have been obtained with Cu II complexes coordinated to bidentate ligands, since they facilitate the approach and the coordination of catechol to the metal. Particularly, the introduction of a thiophenyl group to mimic the sulfur atom at proximity to the catalytic center in the catechol oxidase protein structure improves the catalytic activity of the complex.

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Thiophene-containing dinucleating ligands for the copper-catalyzed oxidative coupling of 2,6-dimethylphenol

Cited by 14 publications

References 20 publications

Catalytic applications of CuII-containing MOFs based on N-heterocyclic ligand in the oxidative coupling of 2,6-dimethylphenol

Catalytic applications of CuII-containing MOFs based on N-heterocyclic ligand in the oxidative coupling of 2,6-dimethylphenol

Dicopper(II) and Dizinc(II) Complexes with Nonsymmetric Dinucleating Ligands Based on Indolo[3,2-c]quinolines: Synthesis, Structure, Cytotoxicity, and Intracellular Distribution

Rate enhancement of the catechol oxidase activity of a series of biomimetic monocopper(ii) complexes by introduction of non-coordinating groups in N-tripodal ligands

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