1579-40-4Relevant academic research and scientific papers
Palladium(II) thiosemicarbazone complex: Synthesis, structure and application to carbon-oxygen cross-coupling reaction
Suganthy, Pandimuni Kalpaga,Prabhu, Rupesh Narayana,Sridevi, Venugopal Shanmugham
, p. 67 - 69 (2014)
A simple route for the synthesis of square-planar palladium(II) 3-methyl-thiophene-2-aldehyde thiosemicarbazone complex is described. The composition of the complex has been established by elemental analysis and spectral methods. The molecular structure was confirmed by single crystal X-ray diffraction study. Further, the complex was used as a potential catalyst for the carbon-oxygen cross-coupling reaction of activating, non-activating and deactivating aryl iodides or aryl bromides with p-cresol.
Tripodal N-heterocyclic carbene complexes of palladium and copper: Syntheses, characterization, and catalytic activity
Ellul, Charles E.,Reed, Graham,Mahon, Mary F.,Pascu, Sofia I.,Whittlesey, Michael K.
, p. 4097 - 4104 (2010)
The tris-palladium tripodal N-heterocyclic carbene (NHC) complexes (timtebtBu){Pd(ICy)I2}3 (4a), (timteb tBu){Pd(PPh3)I2}3 (5a), and (timtebdipp){Pd(PPh3)I2}3 (5b) (timtebtBu = 1,3,5-{tris(tert-butylimidazol-2-ylidene)methyl}-2,4,6- triethylbenzene, 3a; ICy = 1,3-dicyclohexylimidazol-2-ylidene; timteb dipp = 1,3,5-{tris({2,6-diisopropylphenyl}imidazol-2-ylidene)methyl}- 2,4,6-triethylbenzene, 3b) were prepared by reaction of Pd(II) precursors with either the free carbenes or imidazolium salts. Treatment of [Cu(NCMe) 4]X (X = PF6, BF4) with 3a or 3b produced the tris-copper(I) bridged complexes [(timtebR) Cu3(μ3-O)]X (R = tBu, X = PF6, 6a; R = dipp, X = BF4, 6b). Complexes 4a, 5a, and 6a were structurally characterized. The palladium complexes were tested as catalysts for Suzuki-Miyaura and Sonogashira coupling reactions and the copper species also employed for the Sonogashira reaction, as well as for the Ullmann-type arylation of imidazoles and phenols.
Synthesis of diaryl ethers using an easy-to-prepare, air-stable, soluble copper(I) catalyst
Gujadhur,Venkataraman
, p. 2865 - 2879 (2001)
We have found that bromo(triphenylphosphine)copper(I), an air-stable and soluble copper(I) complex, can be used as a catalyst in the synthesis of diaryl ethers. Using this catalyst, we have synthesized diaryl ethers from electron-rich aryl bromides and electron-rich phenols in the presence of cesium carbonate, in 17-24 h, in NMP. We also found that electron-deficient aryl bromides couple with phenols in the presence of cesium carbonate, in 6 h in NMP at 70°C, without the catalyst.
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.
Pd-Catalyzed Etherification of Nitroarenes
Matsushita, Naoki,Kashihara, Myuto,Formica, Michele,Nakao, Yoshiaki
supporting information, p. 2209 - 2214 (2021/07/20)
The Pd-catalyzed etherification of nitroarenes with arenols has been achieved using a new rationally designed ligand. Mechanistic insights were used to design the ligand so that both the oxidative addition and reductive elimination steps of a plausible catalytic cycle were facilitated. The catalytic system established here provides direct access to a range of unsymmetrical diaryl ethers from nitroarenes.
Oxalohydrazide Ligands for Copper-Catalyzed C?O Coupling Reactions with High Turnover Numbers
Ray, Ritwika,Hartwig, John F.
supporting information, p. 8203 - 8211 (2021/03/08)
Here, we report a class of ligands based on oxalohydrazide cores and N-amino pyrrole and N-amino indole units that generates long-lived copper catalysts for couplings that form the C?O bonds in biaryl ethers. These Cu-catalyzed coupling of phenols with aryl bromides occurred with turnovers up to 8000, a value which is nearly two orders of magnitude higher than those of prior couplings to form biaryl ethers and nearly an order of magnitude higher than those of any prior copper-catalyzed coupling of aryl bromides and chlorides. This ligand also led to copper systems that catalyze the coupling of aryl chlorides with phenols and the coupling of aryl bromides and iodides with primary benzylic and aliphatic alcohols. A wide variety of functional groups including nitriles, halides, ethers, ketones, amines, esters, amides, vinylarenes, alcohols and boronic acid esters were tolerated, and reactions occurred with aryl bromides in pharmaceutically related structures.
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
, (2020/04/15)
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).
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.].
Oxalic amide ligands, and uses thereof in copper-catalyzed coupling reaction of aryl halides
-
Page/Page column 98, (2020/01/09)
The present invention provides oxalic amide ligands and uses thereof in copper-catalyzed coupling reaction of aryl halides. Specifically, the present invention provides a use of a compound represented by formula I, wherein definitions of each group are described in the specification. The compound represented by formula I can be used as a ligand in copper-catalyzed coupling reaction of aryl halides for the formation of C—N, C—O and C—S bonds.
Immobilized palladium nanoparticles on MNPs@A-N-AEB as an efficient catalyst for C-O bond formation in water as a green Solvent
Moghaddam, Firouz Matloubi,Eslami, Mohammad
, (2018/08/24)
Palladium nanoparticles immobilized on the magnetic nanoparticles@2-amino-N-(2-aminoethyl) benzamide (MNPs@A-N-AEB.Pd0) have been presented as an efficient, and reusable magnetically heterogeneous catalyst for the C-O coupling reaction, namely Ullmann condensation reactions in an aqueous medium. This heterogeneous catalyst shows superior reactivity for the C-O arylation of different aryl halide (chloride, bromide, and iodide) with phenol derivatives to afford the desired products in good to excellent yields within short reaction time. Moreover, the catalyst can be easily recovered and reused for seven runs without loss of catalytic activity. The catalyst was characterized by several techniques, such as FT-IR, SEM, TEM, EDS, XRD, TGA and ICP-OES.
