40843-46-7Relevant articles and documents
CoII Immobilized on Aminated Magnetic-Based Metal–Organic Framework: An Efficient Heterogeneous Nanostructured Catalyst for the C–O Cross-Coupling Reaction in Solvent-Free Conditions
Mohammadinezhad, Arezou,Akhlaghinia, Batool
, p. 332 - 352 (2020/01/11)
Abstract: In this paper, we report the synthesis of Fe3O4?AMCA-MIL53(Al)-NH2-CoII NPs based on the metal–organic framework structures as a magnetically separable and environmentally friendly heterogeneous nanocatalyst. The prepared nanostructured catalyst efficiently promotes the C–O cross-coupling reaction in solvent-free conditions without the need for using toxic solvents and/or expensive palladium catalyst. Graphic Abstract: [Figure not available: see fulltext.].
Magnetically recyclable nano copper/chitosan in O-arylation of phenols with aryl halides
Mousavi Mashhadi, Seyed Ali,Kassaee, Mohamad Z.,Eidi, Esmaiel
, (2019/07/04)
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.
Cu(I)-PNF, an organic-based nanocatalyst, catalyzed C-O and C-S cross-coupling reactions
Taherinia, Zahra,Ghorbani-Choghamarani, Arash
, p. 46 - 52 (2019/01/10)
Peptide nanofiber has been prepared via a self-assembly protocol and decorated with Cu(I) to prepare a nanostructural catalyst. The catalytic activity of this prepared nanomaterial (Cu(I)-PNF) was examined in C-O and C-S cross-coupling reactions. Compared with conventional copper-ligand catalytic systems, CuNP-PNF has unique advantages such as water solubility, high efficiency, and low cost, which makes it a highly efficient and beneficial catalyst to reuse in cross-coupling reactions.
Copper-Catalyzed Diaryl Ether Formation from (Hetero)aryl Halides at Low Catalytic Loadings
Zhai, Yuntong,Chen, Xiaofei,Zhou, Wei,Fan, Mengyang,Lai, Yisheng,Ma, Dawei
, p. 4964 - 4969 (2017/05/12)
Diaryl formation is achieved by coupling phenols and (hetero)aryl halides under the catalysis of CuI/N,N′-bis(2-phenylphenyl) oxalamide (BPPO) or CuI/N-(2-phenylphenyl)-N′-benzyl oxalamide (PPBO) at 90 °C using DMF or MeCN as the solvent. Only 0.2-2 mol % CuI and ligand are required for complete conversion, which represents the lowest catalytic loadings for a general Cu/ligand-catalyzed diaryl ether formation.
Simple N-Heterocyclic Carbenes as Ligands in Ullmann-Type Ether and Thioether Formations
Wu, Jiang-Ping,Saha, Anjan K.,Haddad, Nizar,Busacca, Carl A.,Lorenz, Jon C.,Lee, Heewon,Senanayake, Chris H.
supporting information, p. 1924 - 1928 (2016/07/06)
A simple N-heterocyclic carbene (NHC) derived from 1-methyl-3-ethylimidazolium tetrafluoroborate was found to be an efficient ligand for a range of copper-catalyzed cross-coupling reactions, leading to the formation of aromatic ethers and thioethers. (Figure presented.) .
CuI/oxalamide catalyzed couplings of (hetero)aryl chlorides and phenols for diaryl ether formation
Fan, Mengyang,Zhou, Wei,Jiang, Yongwen,Ma, Dawei
supporting information, p. 6211 - 6215 (2016/05/24)
Couplings between (hetero)aryl chlorides and phenols can be effectively promoted by CuI in combination with an N-aryl-N′-alkyl-substituted oxalamide ligand to proceed smoothly at 120 °C. For this process, N-aryl-N′-alkyl-substituted oxalamides are more effective ligands than bis(N-aryl)-substituted oxalamides. A wide range of electron-rich and electron-poor aryl and heteroaryl chlorides gave the corresponding coupling products in good yields. Satisfactory conversions were achieved with electron-rich phenols as well as a limited range of electron-poor phenols. Catalyst and ligand loadings as low as 1.5 mol % are sufficient for the scaled-up variants of some of these reactions. Aryl and alkyl: N-Aryl-N′-alkyl-substituted oxalamide ligands promote the CuI catalyzed coupling of (hetero)aryl chlorides and phenols at 120 °C more effectively than bis(N-aryl)-substituted oxalamides. A wide range of electron-rich and electron-poor aryl and heteroaryl chlorides were converted into the corresponding coupling products in good yields.
Copper and l-sodium ascorbate catalyzed hydroxylation and aryloxylation of aryl halides
Song, Guang-Lin,Zhang, Zhang,Da, Yu-Xia,Wang, Xi-Cun
, p. 8823 - 8829 (2015/10/20)
CuSO4·5H2O and NaAsc catalyzed hydroxylation and C-O/C-S cross-coupling reactions of aryl halides with phenols or 4-methylbenzenethiol were described. A wide range of substrates and test cases highlight the synthetic utility of the approach. A series of phenols, diaryl ethers, alkylaryl ethers, and diaryl thioethers were synthesized in high yield.
A highly active and recyclable catalyst for the synthesis of indole and phenyl ether
Qiao, Bo,Zhang, Le,Li, Rong
, p. 93463 - 93469 (2015/11/17)
A new simple catalytic system consisting of copper-aluminium and hydrotalcite (CuAl-HT) has been developed using a facile one-pot method without harm to the environment. The catalyst was characterized using TEM, XRD and XPS. It could be used as an efficient catalyst for the synthesis of both indole and phenyl ether. As expected, the catalyst afforded high catalytic activity for the selective synthesis of indole via intramolecular dehydrogenative N-heterocyclization of 2-(2-aminophenyl)ethanol. Meanwhile, it also exhibited superior catalytic properties for an Ullmann-type coupling reaction to synthesise phenyl ether from iodobenzene and phenol. The CuAl-HT catalyst showed higher activity than conventional catalysts based on copper and could be recycled several times with stable catalytic activity. This procedure has real economic advantages since no expensive materials were used.
Ligand free copper-catalyzed heterogeneous O-arylation reaction under green condition
Maity, Tanmoy,Saha, Debraj,Das, Soma,Bhunia, Susmita,Koner, Subratanath
, p. 141 - 148 (2014/12/10)
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.
Copper-catalyzed Ullmann-type synthesis of diaryl ethers assisted by salicylaldimine ligands
Qian, Cun-Wei,Lv, Wen-Lin,Zong, Qian-Shou,Wang, Mao-Yuan,Fang, Dong
, p. 337 - 340 (2014/02/14)
A series of salicylaldimine ligands were designed to promote the copper-catalyzed Ullmann cross-coupling reaction. After a screening process, 2-((2-isopropylphenylimino)methyl)phenol was found to serve as a good supporting ligand for this reaction. Employing this Schiff-base ligand as a new supporting ligand, the copper-catalyzed coupling reactions of aryl bromides and aryl iodides with various phenols successfully proceeded in good yields under mild conditions. Various diaryl ethers were obtained with excellent yields in dioxane in the presence of K3PO4 and a catalytic amount of copper(I) salt.
