10040-96-7Relevant articles and documents
An efficient route to unsymmetrical bis(azolium) salts: CCC-NHC pincer ligand complex precursors
Box, Hannah K.,Howell, Tyler O.,Kennon, William E.,Burk, Griffin A.,Valle, Henry U.,Hollis, T. Keith
, p. 2191 - 2195 (2017)
The coupling of N-heterocyclic azoles (imidazoles, benzimidazoles, triazoles) to bromobenzenes (1,2-; 1,3-; or 1,4) in a step-wise, sequential manner was accomplished by manipulation of reaction time and stoichiometry, which provided straight-forward acce
Imidazolium- and Triazine-Based Porous Organic Polymers for Heterogeneous Catalytic Conversion of CO2 into Cyclic Carbonates
Zhong, Hong,Su, Yanqing,Chen, Xingwei,Li, Xiaoju,Wang, Ruihu
, p. 4855 - 4863 (2017)
CO2 adsorption and concomitant catalytic conversion into useful chemicals are promising approaches to alleviate the energy crisis and effects of global warming. This is highly desirable for developing new types of heterogeneous catalytic materials containing CO2-philic groups and catalytic active sites for CO2 chemical transformation. Here, we present an imidazolium- and triazine-based porous organic polymer with counter chloride anion (IT-POP-1). The porosity and CO2 affinity of IT-POP-1 may be modulated at the molecular level through a facile anion-exchange strategy. Compared with the post-modified polymers with iodide and hexafluorophosphate anions, IT-POP-1 possesses the highest surface area and the best CO2 uptake capacity with excellent adsorption selectivity over N2. The roles of the task-specific components such as triazine, imidazolium, hydroxyl, and counter anions in CO2 absorption and catalytic performance were illustrated. IT-POP-1 exhibits the highest catalytic activity and excellent recyclability in solvent- and additive-free cycloaddition reaction of CO2 with epoxides.
Magnetic nano-Fe3O4 supported ionic liquids: A recoverable phase transfer catalyst for c-n cross coupling reaction
Tang, Lin,Sun, Yu,Zhou, Lingyun,Shao, Taili
, p. 6240 - 6242 (2013)
Magnetic nanoparticles-supported quaternary ammonium salts were prepared and evaluated as phase transfer catalysts. Some of them exhibited good activities in CuCl-catalyzed N-arylation of aryl amines and N-heterocycles with aryl iodides in aqueous solution without any ligands. They could be readily separated from reaction solution using an external magnet and reused three times with a little loss in activity.
SBA-15 Immobilized Phenanthroline-Copper(I) Complex as a Recyclable Efficient Catalyst for N-Arylation of Amides and N-H Heterocycles with Aryl Halides
Hosseinzadeh, Rahman,Aghili, Nora,Tajbakhsh, Mahmood
, p. 193 - 203 (2016)
5-(N,N-bis-3-(triethoxysilyl) propyl) ureyl-1,10-phenanthroline was prepared and successively grafted onto mesoporous silica of SBA-15 to get SBA-15 anchored ligand which was then reacted with Cu(I) to get SBA-15 anchored complex as the heterogeneous copper catalyst. This catalyst was characterized by FT-IR, XRD, CHN, AAS, TGA, EDAX, BET, SEM and TEM. The activities of the catalyst were tested in C-N cross-coupling of amides and N-H heterocycle compounds with aryl halides. The catalyst showed high catalytic activities for these cross-coupling reactions providing good to excellent yields of desired products. Moreover, the catalyst can be easily recovered by simple filtration and reused several times without significant loss of its catalytic activity.
3D printing of a heterogeneous copper-based catalyst
Tubío, Carmen R.,Azuaje, Jhonny,Escalante, Luz,Coelho, Alberto,Guitián, Francisco,Sotelo, Eddy,Gil, Alvaro
, p. 110 - 115 (2016)
One of the most important environmental challenges of modern society is to develop new catalysts that make possible chemical processes with reduced environmental impact. Catalyst immobilization is an appealing strategy that, in addition to facilitating catalyst recovery, has proved to give higher catalytic performance, since the solid support usually provides chemical, thermal, and mechanical stabilization to the catalytic species. In this work Cu/Al2O3 catalytic system with a woodpile porous structure is synthesized by 3D printing and then sintered at high temperature to generate a copper-supported rigid structure with high mechanical strength, a high surface-to-volume ratio, and controlled porosity. The catalytic species (Cu) are immobilized in the Al2O3 matrix to avoid the leaching of the metal into the reaction medium. Al2O3 was selected because it is a good material to obtain a structure with high mechanical stability after high-temperature treatment. The resulting device shows high catalytic efficacy and good recyclability and did not produce leaching of copper to the reaction medium in different Ullmann reactions. Ease of preparation, excellent reactivity, recyclability, and negligible metal contamination all make the 3D printing technique a good strategy for fabricating other types of metal/oxide heterogeneous catalytic systems.
4,7-Dimethoxy-1,10-phenanthroline: An excellent ligand for the Cu-catalyzed N-arylation of imidazoles
Altman, Ryan A.,Buchwald, Stephen L.
, p. 2779 - 2782 (2006)
4,7-Dimethoxy-1,10-phenanthroline (L) was found to be an efficient ligand for the copper-catalyzed N-arylation of imidazole with aryl iodides and bromides under mild conditions. A variety of hindered and functionalized imidazoles and aryl halides were transformed in good to excellent yields.
The Catalytic Properties of a Copper-Based Nanoscale Coordination Polymer Fabricated by a Solvent-Etching Top-Down Route
Cao, Xiaowei,Fang, Zhenlan,Huang, Wei,Ju, Qiang
, p. 4803 - 4807 (2017)
Manipulating particle size is a powerful means of creating unprecedented applications in both inorganic and organic materials. Coordination polymers, which are emerging as a type of organic–inorganic hybrid materials, have attracted thriving interest in a variety of applications, but nanoscale coordination polymers have scarcely been touched. In this work, the pure-phase {Cu6[1,4-bis(imidazol-1-yl)butane]3I6}∞ coordination polymer with different sizes and morphologies was synthesized for the first time through a facile top-down route assisted by solvent etching. The size and morphology could be adjusted simply by varying the participating etching solvents. Our mechanistic investigations suggest that the bulk coordination polymer as a precursor in the etching solvents may experience a process of dispersion, dissolution, and recrystallization to generate the nanoscale counterpart. High catalytic activity of the nanoscale coordination polymer was observed in the N-arylation of imidazole aryl halides, and this was attributed to a high surface area and a low coordination number of unsaturated coordination sites. This simple and rapid preparation, requiring neither specialized equipment nor harsh conditions, suggests a wealth of potential for reducing the size of coordination polymers to comply with various practical applications.
Mild transition-metal-free amination of fluoroarenes catalyzed by fluoride ions
Dehe, Daniel,Munstein, Isabel,Reis, Andreas,Thiel, Werner R.
, p. 1151 - 1154 (2011)
Trimethylsilyl-protected heterocycles undergo N-C bond formation with a variety of electron-deficient fluoroarenes catalyzed by fluoride ions. This reaction avoids stoichiometric amounts of base and thus makes N-arylheterocycles accessible in a very mild and transition-metal-free way.
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.
Synthesis of some new distyrylbenzene derivatives using immobilized Pd on an NHC-functionalized MIL-101(Cr) catalyst: photophysical property evaluation, DFT and TD-DFT calculations
Niknam, Esmaeil,Mahmoodi, Ali,Panahi, Farhad,Heydari Dokoohaki, Maryam,Zolghadr, Amin Reza,Khalafi-Nezhad, Ali
, p. 12374 - 12380 (2021/04/07)
In this study the catalytic application of a heterogeneous Pd-catalyst system based on metal organic framework [Pd-NHC-MIL-101(Cr)] was investigated in the synthesis of distyrylbenzene derivatives using the Heck reaction. The Pd-NHC-MIL-101(Cr) catalyst s
