1205-71-6Relevant academic research and scientific papers
A facile and practical copper diacetate mediated, ligand free C-N cross coupling of trivalent organobismuth compounds with amines and N-heteroarenes
Jadhav,Pardeshi
, p. 14531 - 14537 (2016)
In present work, an efficient Cu(OAc)2·H2O catalyzed protocol in the absence of any additional ligand has been developed for the N-arylation of amines and nitrogen containing heterocycles using trivalent organobismuth reagents under mild conditions. This protocol tolerates a variety of functional groups on amines and the organobismuth reagent with a high degree of chemoselectivity.
Iron-catalyzed oxidative monoarylation of primary amines with organozinc reagents
Nakamura, Yuki,Ilies, Laurean,Nakamura, Eiichi
, p. 5998 - 6001 (2011)
The reaction of a primary zinc amide with a diorganozinc reagent gives a secondary amine in the presence of Fe(acac)3 as a catalyst and 1,2-dichloroisobutane (DCIB) as an oxidant. Halogen groups such as F, Cl, Br, and I are tolerated well. The dichloride oxidant and heat are essential to achieve the C-N bond formation presumably from a catalytic iron intermediate species bearing aryl and amido groups.
Addition of aryl cuprates to azides: a novel approach for the synthesis of unsymmetrical diaryl amines
Yadav,Reddy, B.V. Subba,Borkar, Prashant,Reddy, P. Janardhan
, p. 6642 - 6645 (2009)
Aryl and benzyl azides react smoothly with aryl cuprates, generated in situ from aryl magnesium bromide and CuCN in THF to furnish a variety of unsymmetrical diaryl amines in good yields. This is the first report on the synthesis of diarylamines from aryl
CuCl2 heterogenized on metformine-modified polystyrene resin as an antibacterial agent and recyclable nanocatalyst for Ullmann-type C-N coupling reactions
Veisi, Hojat,Ahmadian, Hossein,Mirshokraie, Seyed Ahmad,Didehban, Khadijeh,Zangeneh, Mohammad Mahdi
, (2019)
Merrifield Resin was functionalized with metformine and applied as a solid support to immobilize the CuCl2. The Ps-Met/CuCl2 was characterized by several techniques including Fourier transform infrared (FTIR), field emission scanning electron microscopy (FESEM), energy-dispersive X-ray spectroscopy (EDX), wavelength-dispersive X-ray spectroscopy (WDX) and inductively coupled plasma (ICP). The Ps-Met/CuCl2 was used as an efficient recyclable solid nanocatalyst for N-arylation of indole and aniline through coupling reactions of Ullmann-type C-N. The advantages of this method are easy workup, improved yields, and simple recovery via filtration. Ultimately, the Ps-Met/CuCl2 antibacterial property was examined against two bacteria (Staphylococcus aureus (Staph. aureus) and Escherichia coli (E. coli)) and indicated its antibacterial performance against gram negative (E. coli) bacteria and gram positive (Staph. aureus).
Synthesis, characterization and catalytic application of some novel binuclear transition metal complexes of bis-(2-acetylthiophene) oxaloyldihydrazone for CN bond formation
Singh, Divya Pratap,Raghuvanshi, Dushyant S.,Singh,Singh, Vinod P.
, p. 21 - 29 (2013)
In the present work, synthesis, characterization and catalytic properties of some novel complexes derived from a Schiff base bis-(2-acetylthiophene) oxaloyldihydrazone with various transition metal ions and precursors have been reported. The complexes were characterized by IR, NMR, ESR, electronic and mass spectroscopy, magnetic moments and TGA studies. Molecular structures of the ligand and its Cu(I) complex are determined by single crystal X-ray diffraction. Electronic spectral studies exhibit a 6-coordinated geometry around metal centers for Co(II), Ni(II) and Cu(II) complexes, whereas 4-coordinated geometry for Cu(I) and Zn(II) complexes. ESR spectra indicate a distorted octahedral geometry for Cu(II) complex in DMSO frozen solution. The electro-chemical studies of Ni(II) and Cu(II) complexes reveal a metal based reversible redox behavior. The catalytic activity of the complexes has been demonstrated for the cross-coupling of arylboronic acids with various N-nucleophiles. Ni(II) complex exhibited the maximum impact on catalytic activity with the product yields ranging from 62% to 82%.
Cu2(BDC)2(BPY)-MOF: An efficient and reusable heterogeneous catalyst for the aerobic Chan-Lam coupling prepared via ball-milling strategy
Khosravi, Armaqan,Mokhtari, Javad,Naimi-Jamal, Mohammad Reza,Tahmasebi, Sharareh,Panahi, Leila
, p. 46022 - 46027 (2017)
Nanoporous Cu2(BDC)2(BPY)-MOF was used as efficient and reusable heterogeneous catalyst to effect the aerobic cross-coupling of aromatic amines and phenyl boronic acid (Chan-Lam coupling). Ball-milling strategy was utilized for the first as a powerful green and energy-efficient method for the synthesis of this nanoporous metal-organic framework. Certain ratio of metal ion and organic linkers were held to improve the quality of nanostructures. Cu2(BDC)2(BPY) were characterized by X-ray powder diffraction (XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM) and Brunauer-Emmett-Teller (BET) surface area analysis.
A Novel Modified Cross-Coupling of Phenols and Amines Using Dichloroimidazolidinedione (DCID)
Madankar, Kamelia,Mokhtari, Javad,Mirjafary, Zohreh
, p. 1725 - 1729 (2020)
Phenols are considered as an ideal alternative to aryl halides as coupling partners in cross-coupling reactions. In the present work a copper-catalyzed cross-coupling of phenols with various aromatic and aliphatic amines for the synthesis of secondary aryl amines using dichloroimidazolidinedione (DCID) as a new and efficient activating agent has been developed. Substituted phenols were compatible with the standard reaction conditions. The two proposed mechanisms, which are based on the oxidation addition of copper with Ar-OMCID (MCID: Monochloroimidazolidinedione), are also discussed.
N-Arylation of indole and aniline by a green synthesized CuO nanoparticles mediated by Thymbra spicata leaves extract as a recyclable and heterogeneous nanocatalyst
Veisi, Hojat,Hemmati, Saba,Javaheri, Hadis
, p. 3155 - 3159 (2017)
In a biological procedure where the aqueous leaves extract of Thymbra spicata was utilized as a reducing and capping agent, copper oxide (CuO) nanoparticles (NPs) were synthesized. These CuO NPs were characterized via Fourier transformed infrared spectroscopy (FT-IR), X-ray diffraction (XRD), field emission scanning electron microscopy (FE-SEM), transmission electron microscopy (TEM), energy dispersive X-ray spectroscopy (EDS), wavelength-dispersive X-ray spectroscopy (WDX), and UV–visible spectroscopy. The as prepared nanoparticles have been employed as an appropriate nanocatalyst for ligand-free N-arylation of indole and aniline via Ullmann-type C[sbnd]N coupling reactions. Adequate to outstanding quantities of the N-arylated products were synthesized and the nanocatalyst was retrievable and reusable seven times without noticeable decrease in catalytic performance.
Copper nanoparticle anchored biguanidine-modified Zr-UiO-66 MOFs: a competent heterogeneous and reusable nanocatalyst in Buchwald-Hartwig and Ullmann type coupling reactions
Veisi, Hojat,Neyestani, Narges,Pirhayati, Mozhgan,Ahany Kamangar, Sheida,Lotfi, Shahram,Tamoradi, Taiebeh,Karmakar, Bikash
, p. 22278 - 22286 (2021/07/02)
We have designed a functionalized metal-organic framework (MOF) of UiO topology as a support, with an extremely high surface area, adjustable pore sizes and stable crystalline coordination polymeric structure and implanted copper (Cu) nanoparticles thereon. The core three dimensional Zr-derived MOF (UiO-66-NH2) was modified with a biguanidine moiety following a covalent post-functionalization approach. The morphological and physicochemical features of the material were determined using analytical methods such as FT-IR, SEM, TEM, EDX, atomic mapping, XRD and ICP-OES. The SEM and XRD results justified the unaffected morphology of Zr-MOF after structural modifications. The as-synthesized UiO-66-biguanidine/Cu nanocomposite was catalytically explored in the aryl and heteroaryl Buchwald-Hartwig C-N and Ullmann type C-O cross coupling reactions with excellent yields. A library of biaryl amine and biaryl ethers was synthesized over the catalyst under mild and green conditions. Furthermore, the catalyst was isolated by centrifugation and recycled 11 times with no significant copper leaching or change in its activity.
A quinoxaline-based porous organic polymer containing copper nanoparticles CuNPs@Q-POP as a robust nanocatalyst toward C-N coupling reaction
Gorginpour, Forough,Zali-Boeini, Hassan,Rudbari, Hadi Amiri
, p. 3655 - 3665 (2021/02/03)
A novel porous organic polymer (denoted by Q-POP) was successfully fabricated by free-radical copolymerization of allyl-substituted 2,3-di(2-hydroxyphenyl)1,2-dihydroquinoxaline, and divinylbenzene under solvothermal conditions and used as a new platform for immobilization of copper nanoparticles. The CuNPs@Q-POP nanocatalyst was prepared via incorporating of Cu(NO3)2 into the polymeric network, followed by the reduction of Cu2+ ion with hydrazine hydrate. The obtained materials were characterized through FT-IR, XRD, N2 adsorption-desorption isotherms, ICP, TGA, SEM, HR-TEM, EDX, and the single-crystal X-ray crystallography. The results displayed that Q-POP and CuNPs@Q-POP possessed high surface area, hierarchical porosity, and excellent thermal and chemical stability. The as-synthesized catalyst was utilized for the Ullmann C-N coupling reaction of aromatic amines and different aryl halides to prepare various diarylamine derivatives. All types of aryl halides (except aryl fluorides) were screened in the Ullmann C-N coupling reaction with aromatic amines to produce diaryl amines in good to excellent yields (50-98%), and it turned out that aryl iodides have the best results. Besides, due to the strong interactions between CuNPs, N, and O-atoms of quinoxaline moiety existing in the polymeric framework, the copper leaching from the support was not observed. Furthermore, the catalyst was recycled and reused for five consecutive runs without significant activity loss.
