Recent Advances in C–C and C–N Bond Forming Reactions Catalysed by Polystyrene-Supported Copper Complexes

Drabina, Pavel; Svoboda, Jan; Sedlák, Miloš

doi:10.3390/molecules22060865

Cited by 23 publications

(3 citation statements)

References 67 publications

(144 reference statements)

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“…Schiff base copper complexes with various types of ligands have shown to possess effective catalytic ability. [13][14][15] Based on the above catalytic activity importance of Schiff base complexes and in continuation of our recent work [16][17][18][19] on the Schiff base complexes, in the current investigation, two copper(II) complexes with NNOS coordination sphere have been synthesized and characterized. Catalytic potential have also been explored.…”

Section: Introductionmentioning

confidence: 91%

Copper(II) Schiff Base Complexes with Catalyst Property: Experimental, Theoretical, Thermodynamic and Biological Studies

Esmaielzadeh

Zarenezhad

2018

ACSi

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Two novel copper(II) Schiff base complexes were synthesized and characterized by various physico-chemical and spectroscopic methods, revealing a distorted square planar geometry around the copper atom. The analytical data confirmed the 1:1 metal to ligand stoichiometry of the complexes. B3LYP/(LANL2DZ/6-311G**) density functional theory (DFT) were used to investigate structural and electronic properties of the synthesized compounds in gas phase. The computational results support the conclusion obtained by the experimental studies. Thermodynamic study of complex formation in solution was carried out spectrophotometrically at 25 °C. These compounds were also subjected to study in vitro antibacterial screening against some bacteria. Also, click reaction was investigated for its catalytic properties. The synthesized Schiff base copper complexes catalyzed 1,3-dipolar Huisgen cycloaddition of different functionalized ?-azido alcohols and alkynes in the presence of ascorbic acid in a solution of THF/H2O (2:1, V/V) at room temperature.

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Section: Introductionmentioning

confidence: 91%

Copper(II) Schiff Base Complexes with Catalyst Property: Experimental, Theoretical, Thermodynamic and Biological Studies

Esmaielzadeh

Zarenezhad

2018

ACSi

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“…However, electrostatic interaction and hydrogen bonds between stabilizers and metal ions play a vital role in preventing the growth and accumulation of metal in the reaction media. , Currently, most researchers have focused on utilization of eco-friendly, renewable resources and sustainable solid supports and processes that apply to tangible assistance . The solid-supported catalysts, namely, metal-organic framework/covalent organic framework (MOF/COF)-supported, , polystyrene-supported, nonmagnetic- and magnetic-supported, carbon-based, MCM-supported, metal-decorated hyper-cross-linked network, and salen-based hyper-cross-linked polymer catalysts, , showed an extraordinary catalytic ability toward the organic reaction. Nevertheless, they are out of the viewpoint of sustainable protocols in green chemistry principles.…”

Section: Introductionmentioning

confidence: 99%

Highly Active Cellulose-Supported Poly(hydroxamic acid)–Cu(II) Complex for Ullmann Etherification

et al. 2021

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Highly active natural pandanus-extracted cellulose-supported poly(hydroxamic acid)–Cu(II) complex 4 was synthesized. The surface of pandanus cellulose was modified through graft copolymerization using purified methyl acrylate as a monomer. Then, copolymer methyl acrylate was converted into a bidentate chelating ligand poly(hydroxamic acid) via a Loosen rearrangement in the presence of an aqueous solution of hydroxylamine. Finally, copper species were incorporated into poly(hydroxamic acid) via the adsorption process. Cu(II) complex 4 was fully characterized by Fourier transform infrared (FTIR), field emission scanning electron microscopy (FE-SEM), energy-dispersive X-ray (EDX), transmission electron microscopy (TEM), inductively coupled plasma optical emission spectrometry (ICP-OES), thermogravimetric analysis (TGA), X-ray diffraction (XRD), and X-ray photoelectron spectroscopy (XPS) analyses. The cellulose-supported Cu(II) complex 4 was successfully applied (0.005 mol %) to the Ullmann etherification of aryl, benzyl halides, and phenacyl bromide with a number of aromatic phenols to provide the corresponding ethers with excellent yield [benzyl halide (70–99%); aryl halide (20–90%)]. Cu(II) complex 4 showed high stability and was easily recovered from the reaction mixture. It could be reused up to seven times without loss of its original catalytic activity. Therefore, Cu(II) complex 4 can be commercially utilized for the preparation of various ethers, and this synthetic technique could be a part in the synthesis of natural products and medicinal compounds.

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“…One of the powerful synthetic tools for advancement in the preparation of a wide range of chemical molecules including drug molecules is carbon–carbon bond formation . This kind of approach developed significantly in the area of synthetic strategy for a wide range of molecules in both research and industry; these reactions are known as coupling reactions.…”

Section: Introductionmentioning

confidence: 99%

One-Pot Suzuki–Miyaura C–C Coupling Reaction versus Stepwise Reaction Involving Isolated Synthesized Catalyst Addition

Koudehi

Zibaseresht

2020

J. Chem. Educ.

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Suzuki–Miyaura coupling reactions are well-known among the most versatile catalytic C–C bond formation reactions. Two different routes of C–C bond Suzuki–Miyaura coupling reactions for the undergraduate organic chemistry laboratory courses have been designed and explained. A two-step reaction involving a catalyst preparation as the first step and a C–C bond formation as the second step of the reaction was introduced. A one-pot catalytic reaction was also introduced in comparison. The goals for such designation of two different routes for Suzuki–Miyaura cross-coupling reactions were to allow undergraduate students to understand the concept of Suzuki–Miyaura cross-coupling reactions and also to allow the students to experience the ease by which a one-pot reaction can provide a researcher the best way to follow the organic synthesis. During the reactions processes, the students will learn to carry out reactions under a Schlenk line, working with air-sensitive compounds in a glovebox. They will also have the opportunity to compare the reaction approaches in many different ways: for example, cost, time, handling materials, safety, and straightforwardness.

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Recent Advances in C–C and C–N Bond Forming Reactions Catalysed by Polystyrene-Supported Copper Complexes

Cited by 23 publications

References 67 publications

Copper(II) Schiff Base Complexes with Catalyst Property: Experimental, Theoretical, Thermodynamic and Biological Studies

Copper(II) Schiff Base Complexes with Catalyst Property: Experimental, Theoretical, Thermodynamic and Biological Studies

Highly Active Cellulose-Supported Poly(hydroxamic acid)–Cu(II) Complex for Ullmann Etherification

One-Pot Suzuki–Miyaura C–C Coupling Reaction versus Stepwise Reaction Involving Isolated Synthesized Catalyst Addition

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