Xi:Irritant;
101-84-8Relevant articles and documents
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Davis,Golden
, p. 425 (1968)
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A novel magnetic polyacrylonotrile-based palladium Core?Shell complex: A highly efficientcatalyst for Synthesis of Diaryl ethers
Eslami, Mohammad,Jarahiyan, Atefeh,Moghaddam, Firouz Matloubi,Pourjavadi, Ali
, (2020)
The present article describes the synthesis of a new magnetic polyacrylonitrile-based Pd catalyst involving polyacrylonitrile modified via 2-aminopyridine as an efficient support to immobilize Pd nanoparticles. The simple reusability, easy separation and high stability of this Pd complex make it an excellent candidate to generate a C–O bond via Ph-X activation which is a really important subject in achieving biologically active compounds. It is worth to note access to good and high yields as well as broad substrate scope have resulted from superior reactivity of this catalyst complex. Furthermore, the structure of the magnetic polyacrylonitrile-based heterogeneous catalyst was characterized by fourier transmission infrared (FT-IR) spectroscopy, field emission scanning electron microscopy (FE-SEM) and transmission electron microscopy (TEM), X-ray diffraction (XRD). Also, its thermal properties were studied by thermogravimetric analysis (TGA).
Ligand-free catalytic system for the synthesis of diarylethers over Cu 2O/Cu-CNTs as heterogeneous reusable catalyst
Zhang, Ying-Peng,Jiao, Ya-Cong,Yang, Yun-Shang,Li, Chun-Lei
, p. 6494 - 6497 (2013)
Various substituted diarylether derivatives were prepared by using heterogeneous reusable Cu2O- and Cu-coated carbon nanotubes (Cu 2O/Cu-CNTs) as catalyst under ligand-free conditions, which provided good to excellent yields. The catalyst was characterized by TEM, XRD, and AAS analysis. The effects of solvent, base, and amount of catalyst for the O-arylation were investigated. The catalyst could be recovered by simple filtration from the reaction mixture without further treatment and reused several times with consistent catalytic activity. In addition, CNTs could also be recovered from the used Cu2O/Cu-CNTs by a simple acid treatment.
Carbon dioxide thermal system: An effective method for the reduction of carbon dioxide
Chen,Qian
, p. 1402 - 1403 (2001)
When carbon dioxide is in the supercritical state and reduced by Fe3O4, multicarbon bearing hydrocarbon molecules such as phenol (rather than CO or formate usually formed in electrochemical or photochemical techniques) can be obtaine
Ullmann Reaction Catalyzed by Heterogeneous Mesoporous Copper/Manganese Oxide: A Kinetic and Mechanistic Analysis
Mullick, Kankana,Biswas, Sourav,Kim, Chiho,Ramprasad, Ramamurthy,Angeles-Boza, Alfredo M.,Suib, Steven L.
, p. 10290 - 10297 (2017)
A heterogeneous copper oxide supported on mesoporous manganese oxide (meso Cu/MnOx) was explored for Ullmann-type cross-coupling reactions. An inverse micelle-templated evaporation-induced self-assembly method with in situ addition of copper was adopted to synthesize the mesoporous catalyst. Broad substrate scope and excellent functional group tolerability in C-O, C-N, and C-S bond formation reactions were observed using the optimized reaction conditions. The catalytic protocol was ligand free, and the catalyst was reusable without any significant loss of activity. The kinetic and Hammett analyses provided evidence for oxidative addition to a Cu(I) reaction center followed by nucleophilic addition and reductive elimination at the active copper oxide surface. Rate acceleration was observed for aryl halides with electron-withdrawing groups. The Hammett analysis determined ρ = +1.0, indicative of an oxidative addition, whereas the electronic effect in the phenol ring (ρ = -2.9) was indicative of coordination to a metal ion. Theoretically, the oxidative addition of the aryl halides is assisted by the ligand environment of the copper center. Relevant mechanistic implications are discussed on the basis of the experimental and computational results.
The Transition-metal Catalyzed Dehalogenation of Aromatic Halides by NaOH-Alcohols. A Facile Method of Destroying Aromatic Polyhalides
Okamoto, Tadashi,Oka, Shinzaburo
, p. 1265 - 1266 (1981)
Aromatic halides are dehalogenated by heating with NaOH in alcoholic solvents in the presence of transition metal salts, such as rhodium(III) chloride or palladium(II) acetate and triphenylphosphine.Bis(pentabromophenyl) ether was converted into diphenyl ether in 2-propanol when treated for 5 h at 355 K with a catalytic cycle of more than 80.
Tris-(2-aminoethyl) amine as a novel and efficient tripod ligand for a copper(I)-catalyzed C-O coupling reaction
Jogdand, Nivrutti R.,Shingate, Bapurao B.,Shingare, Murlidhar S.
, p. 4019 - 4021 (2009)
We have introduced a novel, efficient, commercially available and economically attractive N-donor tripod ligand, tris-(2-aminoethyl)amine for copper-catalyzed Ullmann diaryl ether synthesis. This catalyst system is highly active for both aryl iodides and aryl bromides. Variously substituted diaryl ethers have been synthesized in good to excellent yields.
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Gilman,Eidt
, p. 2633,2635, 3848 (1956)
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Ullmann,Sponagel
, (1906)
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Highly efficient copper-catalyzed O-arylation using readily available (S)-N-methylpyrrolidine-2-carboxamide as the ligand
Liu, Xianghao,Fu, Hua,Jiang, Yuyang,Zhao, Yufen
, p. 221 - 224 (2008)
A highly efficient and readily available catalyst system for O-arylation of various phenols using CuI and (S)-N-methylpyrrolidine-2-carboxamide (Pro-NHMe) was developed. The reaction is widely applicable to the synthesis of diaryl ethers. Georg Thieme Verlag Stuttgart.
A recyclable heterogeneous copper(II) Schiff base catalyst for the O-arylation reaction of phenols with aryl halides
Islam, Manirul,Mondal,Mondal,Roy,Mobarak,Hossain
, p. 170 - 174 (2010)
Immobilisation of copper acetate onto a modified polystyrene provided a polymer-supported copper(II) Schiff base catalyst, which is effective in the O-arylation reaction of phenols with aryl halides to give diaryl ethers in high yields. This catalyst is air-stable and was recycled for five times with minimal loss of activity.
Whitesides et al.
, p. 2829,2830 (1974)
Evidence for weak base site participation in the vapour phase methylation of catechol over solid base catalysts
Vishwanathan,Ndou,Sikhwivhilu,Plint,Raghavan,Coville
, p. 893 - 894 (2001)
The vapour phase alkylation of catechol over supported caesium catalysts gives good selectivity to guaiacol formation, and TPD studies indicate that this result can be correlated with the presence of weak basic sites on the catalyst.
Ogata et al.
, p. 2703,2708 (1970)
Impregnated copper on magnetite as catalyst for the O-arylation of phenols with aryl halides
Zhang, Ying-Peng,Shi, Ai-Hong,Yang, Yun-Shang,Li, Chun-Lei
, p. 141 - 145 (2014)
Nanoparticle Fe3O4 encapsulated CuO, as a heterogeneous catalyst, is a facile system for the synthesis of diaryl ethers by the cross-coupling reaction of various substituted aryl halides with various substituted phenols, which avoids using any type of expensive ligand and can be recovered from the reaction mixture by using a simple magnet. Moreover, this catalyst can be reused three times with high catalytic activity.
Synthesis of diaryl ethers by CuI-catalyzed C-O bond formation via Ullman coupling: Assessing the reactivity of aryl halides
Xuesheng Zhang,Liu, Fu,Wei, Zhongbo,Wang, Zunyao
, p. 31 - 36 (2013)
Using cuprous iodide as the catalyst, aryl halides reacted with phenols to form diaryl ethers. The reaction conditions were optimized: aryl halides (1 equiv) reacted with phenol (1 equiv) at 130 °C in DMF for 16 h with cuprous iodide (10 mol %), cesium carbonate (2.5 equiv) as the base, and tetramethylenediamine (5 mol %) as the ligand. Under the optimum conditions, reaction conversion with time was summarized. The structural parameters of four types of aryl halides and the ionization energy of various C-X bond lengths in all aryl halides-CuI π-complexes were calculated at the B3LYP/LANL2MB level by using the Gaussian 03 program and the corresponding Ullman reaction conversion was determined by HPLC. Results suggested that different relationships existed between reactivity and the energy of the lowest unoccupied molecular orbital ELUMO, mean polarizability and dipole moment μ. Both experimental and theoretical results, all displayed Ullman coupling reactivity order of the four aryl halides: fluorobenzene ? chlorobenzene bromobenzene iodobenzene.
Copper-catalyzed etherification of aryl iodides using KF/Al 2O3: An improved protocol
Hosseinzadeh, Rahman,Tajbakhsh, Mahmood,Mohadjerani, Maryam,Alikarami, Mohammad
, p. 1101 - 1104 (2005)
A simple and efficient method for the coupling of aryl iodides with aliphatic alcohols and phenols that does not require the use of alkoxide bases is described. This C-O bond forming procedure shows that the combination of air stable CuI and 1,10-phenanthroline in the presence of KF/Al2O 3 comprises an extremely efficient and general catalyst system for the etherification of aryl iodides. Different functionalized aryl iodides were coupled with alcohols and phenols using this method.
Imafuku
, p. 1684 (1975)
Open air O-arylation reaction of phenols with aryl halides catalyzed by polymer-anchored copper(II) complexes
Islam, Manirul,Mondal, Sanchita,Mondal, Paramita,Roy, Anupam Singha,Hossain, Dildar,Mobarak, Manir
, p. 1 - 11 (2011)
Two copper complexes were synthesized from macroporous chloromethylated polystyrene beads. The first one was prepared by sequential attachment of imidazole and copper acetate with chloromethylated polystyrene-divinyl benzene copolymer, and the second one was prepared from 4-vinylpyridine and copper acetate with chloromethylated polystyrene-divinyl benzene copolymer. These catalysts showed excellent catalytic activity in O-arylation reaction of aryl halides with phenol in dimethylsulfoxide using potassium carbonate at 130 °C under open air conditions to give diaryl ethers in high yields. Less reactive aryl bromides and aryl chlorides have also been shown to react with phenols to give good yields of the diaryl ethers. The effects of various parameters such as solvent, catalyst from different copper salt and base on the reaction system were studied. The reaction is applicable to a wide variety of substituted aryl halides and phenols with different steric and electronic properties. These catalysts were recovered by simple filtration, and the reusability experiments showed that these catalysts can be used five times without much loss in the catalytic activity.
Barberry fruit extract assisted in situ green synthesis of Cu nanoparticles supported on a reduced graphene oxide-Fe3O4 nanocomposite as a magnetically separable and reusable catalyst for the O-arylation of phenols with aryl halides under ligand-free conditions
Nasrollahzadeh, Mahmoud,Maham, Mehdi,Rostami-Vartooni, Akbar,Bagherzadeh, Mojtaba,Sajadi, S. Mohammad
, p. 64769 - 64780 (2015)
In situ synthesis of copper nanoparticles (NPs) supported on a reduced graphene oxide (RGO)-Fe3O4 nanocomposite was carried out with barberry fruit extract as a reducing and stabilizing agent. The morphology and structure of the Cu/RGO-Fe3O4 nanocomposite was fully characterized by means of X-ray diffraction (XRD), Fourier transformed infrared (FT-IR) spectroscopy, field emission scanning electron microscopy (FE-SEM), Raman, energy dispersive X-ray spectroscopy (EDS) and transmission electron microscopy (TEM). Cu/RGO-Fe3O4 was a promising catalyst for the O-arylation of phenols with aryl halides under ligand-free conditions. A diverse range of diaryl ethers were obtained in a good to high yield. Furthermore, due to the magnetic separability and high stability of the composite the catalyst could be separated conveniently from the reaction mixtures by an external permanent magnet and recycled multiple times without loss of catalytic activity.
CuI-USY as a Ligand-Free and Recyclable Catalytic System for the Ullmann-Type Diaryl Ether Synthesis
Magné, Valentin,Garnier, Tony,Danel, Mathieu,Pale, Patrick,Chassaing, Stefan
, p. 4494 - 4497 (2015)
The catalytic potential of copper(I)-exchanged zeolites was evaluated in the Ullmann-type synthesis of diaryl ethers. Among four investigated zeolites (i.e., USY, MOR, β, and ZSM5), CuI-USY was the best catalyst and proved efficient under ligand-free conditions in toluene at 120 °C. CuI-USY was also easy to recover and was recyclable up to five times without significant loss of activity.
A green approach for arylation of phenols using iron catalysis in water under aerobic conditions
Sindhu, Kallikkakam S.,Ujwaldev, Sankuviruthiyil M.,Keerthi Krishnan,Anilkumar, Gopinathan
, p. 146 - 150 (2017)
The first efficient iron-catalyzed coupling of aryl iodides with phenols was developed exclusively with water as solvent. The reaction is performed with low cost and readily available FeCl3·6H2O and DMEDA catalytic system providing diaryl ethers in good to excellent yields. The effectiveness of this reaction was further revealed by compatibility with a wide range of functional groups. Moreover, the procedure is rendered simple as this transformation is carried out in the presence of air. Thus, the protocol represents a facile, economical and eco-friendly procedure to access diaryl ethers.
Mild conditions for copper-catalyzed coupling reaction of phenols and aryl iodides and bromides
Ouali, Armelle,Spindler, Jean-Francis,Cristau, Henri-Jean,Taillefer, Marc
, p. 499 - 505 (2006)
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.
Immobilization of copper in organic-inorganic hybrid materials: a highly efficient and reusable catalyst for the Ullmann diaryl etherification
Miao, Tao,Wang, Lei
, p. 95 - 99 (2007)
The immobilization of copper in organic-inorganic hybrid materials catalyzing the Ullmann reaction has been described. Phenols reacted with aryl iodides, aryl bromides and aryl chlorides smoothly in the presence of a 3-(2-aminoethylamino)propyl functionalized silica gel immobilized copper catalyst. The protocol involved the use of DMSO as the solvent, and potassium fluoride as the base. The reactions generated the corresponding cross-coupling products in good to excellent yields. Furthermore, the silica-supported copper could be recovered and recycled by a simple filtration of the reaction solution and used for 10 consecutive trials without loss of its reactivity.
Ligand free copper-catalyzed heterogeneous O-arylation reaction under green condition
Maity, Tanmoy,Saha, Debraj,Das, Soma,Bhunia, Susmita,Koner, Subratanath
, p. 141 - 148 (2014)
A highly porous Zn-based iso-reticular metal-organic framework (IRMOF-3) has been selected for covalent modification. Pyridine-2-aldehyde has been used to decorate the free amine group of IRMOF-3 in the porous matrix. Schiff base moiety thus generated has been availed to anchor copper(II) ions to prepare the desired catalyst that catalyzes O-arylation reactions heterogeneously under mild reaction conditions. Porous catalyst demonstrates size selectivity in products when various substrates undergo O-arylation with α and β-naphthol.
Synthesis and characterization of nano-cellulose immobilized phenanthroline-copper (I) complex as a recyclable and efficient catalyst for preparation of diaryl ethers, N-aryl amides and N-aryl heterocycles
Aghili, Nora,Hosseinzadeh, Rahman,Mavvaji, Mohammad
, (2022/01/03)
Functionalized nanocellulose was prepared and employed for immobilization of phenanthroline-copper(I) complex to afford cellulose nanofibril grafted heterogeneous copper catalyst [CNF-phen-Cu(I)]. This nanocatalyst was well characterized using FT-IR, NMR, XRD, CHNS, AAS, TGA, EDX and SEM. The activities of the synthesized catalyst were examined in the synthesis of diaryl ethers via C-O cross-coupling of phenols and aryl iodides, as well as, the preparation of N-aryl amides and N-aryl heterocycles through C-N cross-coupling of amides and N-H heterocycle compounds with aryl halides. In this trend, various substrates containing electron-donating and electron-withdrawing groups were exploited to evaluate the generality of this catalytic protocol. Accordingly, the catalyst demonstrated remarkable catalytic efficiency for both C-N and C-O cross-coupling reactions, thereby resulting in good to excellent yields of the desired products. Furthermore, the recoverability experiments of the catalyst showed that it can be readily retrieved by simple filtration and successfully reused several times with negligible loss of its catalytic activity.
Magnetization of graphene oxide nanosheets using nickel magnetic nanoparticles as a novel support for the fabrication of copper as a practical, selective, and reusable nanocatalyst in C-C and C-O coupling reactions
Hajjami, Maryam,Moradi, Parisa
, p. 25867 - 25879 (2021/08/09)
Catalyst species are an important class of materials in chemistry, industry, medicine, and biotechnology. Moreover, waste recycling is an important process in green chemistry and is economically efficient. Herein, magnetic graphene oxide was synthesized using nickel magnetic nanoparticles and further applied as a novel support for the fabrication of a copper catalyst. The catalytic activity of supported copper on magnetic graphene oxide (Cu-ninhydrin@GO-Ni MNPs) was investigated as a selective, practical, and reusable nanocatalyst in the synthesis of diaryl ethers and biphenyls. Some of the obtained products were identified by NMR spectroscopy. This nanocatalyst has been characterized by atomic absorption spectroscopy (AAS), scanning electron microscopy (SEM), wavelength dispersive X-ray spectroscopy (WDX), energy-dispersive X-ray spectroscopy (EDS), X-ray diffraction (XRD), thermogravimetric analysis (TGA), Fourier transform infrared spectroscopy (FT-IR), and vibrating sample magnetometer (VSM) techniques. The results obtained from SEM shown that this catalyst has a nanosheet structure. Also, XRD and FT-IR analysis show that the structure of graphene oxide and nickel magnetic nanoparticles is stable during the modification of the nanoparticles and synthesis of the catalyst. The VSM curve of the catalyst shows that this catalyst can be recovered using an external magnet; therefore, it can be reused several times without a significant loss of its catalytic efficiency. The heterogeneity and stability of this nanocatalyst during organic reactions was confirmed by the hot filtration test and AAS technique.
L-Proline N-oxide dihydrazides as an efficient ligand for cross-coupling reactions of aryl iodides and bromides with amines and phenols
Ding, Zhiqiang,Nie, Nan,Chen, Tian,Meng, Lingxin,Wang, Gongshu,Chen, Zhangpei,Hu, Jianshe
supporting information, (2020/12/21)
A novel catalytic system based on L-proline N-oxide/CuI was developed and applied to the cross-coupling reactions of various N- and O- nucleophilic reagents with aryl iodides and bromides. This strategy featured in the employment of an-proline derived dihydrazides N-oxide compound as the superior supporting ligand. By using this protocol, a variety of products, including N-arylimidazoles, N-arylpyrazoles, N-arylpyrroles, N-arylamines, and aryl ethers, were synthesized with up to 99% yield.
