- Copper(I)–creatine complex on magnetic nanoparticles as a green catalyst for N- and O-arylation in deep eutectic solvent
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Immobilization of copper(I) ions on magnetic nanoparticles was performed using surface modification of Fe3O4 with creatine. Fe3O4?creatine-Cu(I) magnetic catalyst was synthesized and applied in C&bond;X cross-coupling reactions with aryl halides in a deep eutectic as a green solvent. The results indicate the Fe3O4?creatine-Cu(I) magnetic nanoparticles showed excellent activity and high stability. In addition, it was revealed that this catalyst can be recycled five times without significant loss in catalytic activity.
- Bagheri, Sepideh,Heydari, Akbar,Pazoki, Farzane,Radfar, Iman
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- Fe3O4@SiO2-copper sucrose xanthate as a green nanocatalyst for N-, O- and S-arylation
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Formation of C(sp2)–X bonds was carried out using a Fe3O4@SiO2-copper(I) sucrose xanthate nanoparticle catalyst with the aid of the copper(I) xanthate moiety in the catalyst which was prepared from the reaction between sucrose and carbon disulfide through an alkaline medium via the traditional Zeise approach. Various techniques were employed for the characterization of these novel nanoparticles. Three sorts of heteroatoms, N, O and S, successfully underwent heteroatom arylation to produce secondary or tertiary amines, ethers and thioethers, respectively.
- Radfar, Iman,Kazemi Miraki, Maryam,Esfandiary, Naghmeh,Ghandi, Leila,Heydari, Akbar
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- Magnetically recyclable nano copper/chitosan in O-arylation of phenols with aryl halides
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Interaction of chitosan (CS) with Fe3O4, followed by embedding Cu nanoparticles (NPs) on the magnetic surface through adsorption of Cu2+, and its reduction to Cuo via NaBH4, offers a reusable efficient catalyst (Fe3O4/CS-Cu NPs) that is employed in cross-coupling reactions of aryl halides with phenols, which affords the corresponding diaryl ethers, with good to excellent yields. The catalyst is completely recoverable from the reaction mixture by using an external magnet. It can be reused four times, without significant loss in its catalytic activity.
- Mousavi Mashhadi, Seyed Ali,Kassaee, Mohamad Z.,Eidi, Esmaiel
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- Ullmann diaryl ether synthesis catalyzed by copper (I)/pyridine-functionalized silane
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Ullmann-type diaryl ether synthesis was performed under mild conditions in DMF/K2CO3using a pyridinefunctionalized silane as a ligand. The productswere obtained in good yields. This method tolerates a variety of functional groups and is effective in the synthesis of hindered diaryl ethers and heteroaryl ethers.
- Zhang, Baohua,Shi, Lanxiang,Guo, Ruixia,Liu, Sijie
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p. 930 - 932
(2016/07/06)
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- Copper-mediated synthesis of mono- and dichlorinated diaryl ethers
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An efficient synthesis of polychlorinated diphenyl ethers (PCDEs) using the Cu(OAc)2-catalyzed Chan-Lam coupling reaction is described. A library of all possible mono- and dichlorinated diphenyl ether congeners was prepared and characterized using MS, 1H, and 13C NMR spectroscopy, and Kovats retention indices. Our approach, using the optimized reaction conditions (i.e., reaction temperature, oxidizing atmosphere and base), significantly improves and simplifies the process compared to previously reported syntheses.
- ?ermák, Jan K.,Církva, Vladimír
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supporting information
p. 4185 - 4188
(2014/07/22)
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- Nitrogen ligands in copper-catalyzed arylation of phenols: Structure/activity relationships and applications
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In spite of the importance of ligand/ copper-catalyzed arylations of nucleophiles in organic chemistry, the structural and electronic features that make a ligand efficient in these reactions have not been determined until now. In this work, several bident
- Ouali, Armelle,Spindler, Jean-Francis,Jutand, Anny,Taillefer, Marc
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p. 1906 - 1916
(2008/09/17)
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- Mild conditions for copper-catalyzed coupling reaction of phenols and aryl iodides and bromides
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Coupling of phenols and aryl bromides can be efficiently performed by means of catalytic amounts of copper iodide and the inexpensive ligand 1 (structure given in Table 1). The reaction is applicable to a wide range of substrates and proceeds at 60-80 deg;C, the lowest temperatures reported to date for an Ullmann-type synthesis of diaryl ethers. Moreover, the use of aryl bromides and inexpensive K3PO4 as base make this method attractive for applications on an industrial scale.
- Ouali, Armelle,Spindler, Jean-Francis,Cristau, Henri-Jean,Taillefer, Marc
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p. 499 - 505
(2007/10/03)
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- A general and mild Ullmann-type synthesis of diaryl ethers
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(Equation presented) An efficient method for the synthesis of diaryl ethers under particularly mild conditions is described. Inexpensive ligands were found to greatly accelerate the Ullmann-type coupling of aryl bromides or iodides with phenols. A series of diaryl ethers were obtained with excellent yields in acetonitrile in the presence of Cs2CO3 and catalytic copper(I) oxide. The reaction tolerates substrates with unfavorable substitution patterns, such as sterically hindered coupling partners or electron-rich aryl halides.
- Cristau, Henri-Jean,Cellier, Pascal P.,Hamada, Samy,Spindler, Jean-Francis,Taillefer, Marc
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p. 913 - 916
(2007/10/03)
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- Synthesis, structure, and thermal destruction of aroxytetraphenylstiboranes
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A series of aroxytetraphenylstiboranes, Ph4SbOAr, were obtained by the reaction of pentaphenylstiborane with phenols at ca.20 deg C.The thermolysis of these compounds gives O- or o-C-phenylation products.The thermolysis of stiboranes, which incorporate aryl groups containing electron-withdrawing substituents (Ar = 2,4-Br2, 2,4-Cl2, 2-NO2, 4-OPh) produces predominantly simple diaryl ethers of asymmetric structure in 58percent, 90percent, 32percent, and 60percent yields, respectively.
- Sharutin, V. V.,Zhidkov, V. V.,Muslin, D. V.,Liapina, N. Sh.,Fukin, G. K.,et al.
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p. 931 - 936
(2007/10/02)
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