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Ionic liquid mediated Cu-catalyzed cascade oxa-Michael-oxidation: Efficient synthesis of flavones under mild reaction conditions

Flavonoids are a class of natural products, found in a wide range of vascular plants and dietary components. Their low toxicity and extensive biological activities, including anti-cancer and anti-bacterial, have made them attractive candidates to serve as therapeutic agents for many diseases. Herein, we disclose a highly efficient synthetic method of CuI-catalyzed cascade oxa-Michael-oxidation, using chalcones as substrates, mediated by the ionic liquid [bmim][NTf2] at a low temperature. This efficient synthetic method has demonstrated high synthetic utility and can afford flavones in good to high yields (up to 98%).

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Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

 

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Magnetic, Spectral and Thermal Studies on Some Mixed Ligand Complexes of Copper(II) and Nickel(II)

Several mixed ligand complexes of copper(II) and nickel(II) having the compositions and , where aaH is acetylacetone, tcaH is trichloroacetic acid; L is gamma-picoline, imidazole, 2-picoline-N-oxide or thiourea and M is Cu(II) or Ni(II), have been isolated and characterised on the basis of their analyses, molar conductance, magnetic susceptibility, infrared, electronic spectral data and thermogravimetric measurements.The infrared spectra reveal the presence of uninegative bidentate acetyl acetonate and trichloroacetate groups in all these complexes.As the temperature increases, the mixed ligand complexes start decomposing with the loss of neutral donor ligand, followed by trichloroacetate ion and acetylacetonate ion in definite steps and ultimately forming MO at 600-675 deg .Square planar, tetrahedral, distorted octahedral and octahedral structures have been proposed for the complexes, , , and , respectively.

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Reference£º
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

 

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Mechanism and Models for Copper Mediated Nucleophilic Aromatic Substitution. 2. A Single Catalytic Species from Three Different Oxidation States of Copper in an Ullmann Synthesis of Triarylamines

Ullmann condensations of diarylamines with iodobenzenes has been investigated under homogeneous and a heterogeneous catalytic conditions with cupruos and cupric salts, as well as powered copper metal.Copper catalyzed condensation of diarylamines with iodoaromatics is relatively insensitive to substituent (for substituted iodobenzenes p=-0.25; for substituted diphenylamines p=1.09) but quite sensitive to halogen (k1/kBr.200).The first direct evidence for solution catalysis after filtration of a metal catalyzed reactions was obtained.Quantitative analysis of reaction rates, product yields, and catalyst characteristics leads to a comprehensive picture of the formation of soluble cuprous ions as the single active catalytic species under all conditions investigated.This hypothesis rationalizes many of the perplexing results which typify the literature associated with copper catalyzed nucleophilic aromatic substitution.

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Reference£º
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

 

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Crystal phase-controlled synthesis of Cu2FeSnS4 nanocrystals with a band gap of around 1.5 eV

Cu2FeSnS4 (CFTS) nanocrystals with tunable crystal phase have been synthesized using a solution-based method. As-synthesized CFTS nanocrystals in the shape of oblate spheroid and triangular plate with band gaps of 1.54 ¡À 0.04 and 1.46 ¡À 0.03 eV, respectively, appear attractive as a low-cost substitute for thin film solar cells. The Royal Society of Chemistry 2012.

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Reference£º
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

 

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Simultaneous phase and size control in the synthesis of Cu 2SnS3 and Cu2ZnSnS4 nanocrystals

Facile and rapid one-pot synthesis of nearly monodisperse Cu 2SnS3 and Cu2ZnSnS4 nanocrystals was developed using a heating up method. Their crystalline phase and size were simultaneously controlled by judiciously choosing the sulfur precursor reactivity and the oleic acid content. This journal is the Partner Organisations 2014.

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Reference£º
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

 

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Bridging homogeneous and heterogeneous catalysis with MOFs: Cu-MOFs as solid catalysts for three-component coupling and cyclization reactions for the synthesis of propargylamines, indoles and imidazopyridines

Copper-containing MOFs are found to be active, stable and reusable solid catalysts for three-component couplings of amines, aldehydes and alkynes to form the corresponding propargylamines. Two tandem reactions, including an additional cyclization step, leads to the effective production of indoles and imidazopyridines. In particular, the lamellar compound [Cu(BDC)] (BDC = benzene dicarboxylate) is highly efficient for the preparation of imidazopyridines, although a progressive structural change of the solid to a catalytically inactive compact structure is produced, causing deactivation of the catalyst. Nevertheless, the phase change can be reverted by refluxing in DMF, which recovers the original lamellar structure and the catalytic activity of the fresh material. The use of [Cu(BDC)] for this reaction also prevents the formation of Glaser/Hay condensation products of the alkyne, even when the reaction is performed in air atmosphere. This is a further advantage of [Cu(BDC)] with respect to other homogeneous copper catalysts, for which the use of an inert atmosphere is necessary.

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Reference£º
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

 

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Copper catalyzed oxidative coupling of ortho-vinylanilines with N-tosylhydrazones: Efficient synthesis of polysubstituted quinoline derivatives

Efficient and general copper catalyzed oxidative cyclization of ortho-vinylaniline has been accomplished employing N-tosylhydrazone as coupling partner. Various substituted quinoline derivatives of biological importance were achieved in good to excellent yield. The important features are the high functional group tolerates, up-gradation to gram scale synthesis and possible one-pot synthesis of quinoline from corresponding carboxaldehyde. Synthetic potential of the obtained quinoline derivatives was demonstrated through C-H bond functionalization reaction. Furthermore, preliminary mechanistic investigation revealed the possible generation of non-stabilized diazo compound and imine derivative as potential intermediates as well as copper catalyzed electrocyclic reaction and oxidative aromatization.

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Reference£º
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

 

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Homogeneous and heterogeneous catalytic oxidation of benzylic and secondary alcohols with a metal dioxygenato complex in the presence of 2-methylpropanal and dioxygen

The oxidation of benzylic and secondary alcohols under homogeneous conditions was achieved at 40C using molecular oxygen as the oxidant in the presence of excess 2-methylpropanal and catalytic amount of Co(acac)2. The oxidation reactions were also carried out with a heterogeneous analogue of Co(acac)2 revealing that the supported cobalt polymer acts as an active and reusable catalyst.

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Reference£º
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

 

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Synthesis of Cu2O coated Cu nanoparticles and their successful applications to Ullmann-type amination coupling reactions of aryl chlorides

We synthesized uniform Cu2O coated Cu nanoparticles from the thermal decomposition of copper acetylacetonate followed by air oxidation and used these nanoparticles as catalysts for Ullmann type amination coupling reactions of aryl chlorides.

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Reference£º
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

 

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Copper thin films prepared by chemical vapour deposition from copper (II) acetylacetonate

Copper thin films were prepared by a low-temperature atmospheric pressure chemical vapour deposition method. The raw material was copper (II) acetylacetonate. At a reaction temperature above 220 C, polycrystalline copper films can be obtained by hydrogen reduction of the raw material. The resistivity of the film was close to that for bulk copper.

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Reference£º
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”