108-45-2Relevant articles and documents
Magnetic nanoparticle-tethered Schiff base–palladium(II): Highly active and reusable heterogeneous catalyst for Suzuki–Miyaura cross-coupling and reduction of nitroarenes in aqueous medium at room temperature
Manjunatha,Koley, Tuhin S.,Kandathil, Vishal,Dateer, Ramesh B.,Balakrishna, Geetha,Sasidhar,Patil, Shivaputra A.,Patil, Siddappa A.
, (2018)
As a continuation of our efforts to develop new heterogeneous nanomagnetic catalysts for greener reactions, we identified a Schiff base–palladium(II) complex anchored on magnetic nanoparticles (SB-Pd@MNPs) as a highly active nanomagnetic catalyst for Suzuki–Miyaura cross-coupling reactions between phenylboronic acid and aryl halides and for the reduction of nitroarenes using sodium borohydride in an aqueous medium at room temperature. The SB-Pd@MNPs nanomagnetic catalyst shows notable advantages such as simplicity of operation, excellent yields, short reaction times, heterogeneous nature, easy magnetic work up and recyclability. Characterization of the synthesized SB-Pd@MNPs nanomagnetic catalyst was performed with various physicochemical methods such as attenuated total reflectance infrared spectroscopy, UV–visible spectroscopy, inductively coupled plasma atomic emission spectroscopy, energy-dispersive X-ray spectroscopy, field-emission scanning electron microscopy, transmission electron microscopy, powder X-ray powder diffraction, thermogravimetric analysis and Brunauer–Emmett–Teller surface area analysis.
The novel reduction systems: NaBH4-SbCl3 or NaBH4-BiCl3 for conversion of nitroarenes to primary amines
Ren,Pan,Dong,Wu
, p. 3799 - 3803 (1995)
Nitroarenes can be conveniently reduced to primary amines in good to excellent yields by sodium borohydride in the presence of bismuth chloride or antimony chloride.
NiO-Al2O3 prepared from a Ni-Al hydrotalcite precursor as an efficient catalyst for transfer hydrogenation reactions
Jyothi,Raja,Talawar,Sreekumar,Sugunan,Rao
, p. 1573 - 1579 (2000)
NiO-Al2O3 catalyst prepared by calcining a Ni-Al hydrotalcite precursor efficiently reduces nitroarenes and carbonyl compounds in presence of propan-2-ol and KOH. Presence of two different reducible groups in the substrate leads to chemoselective reduction.
Efficient reduction of nitro compounds and domino preparation of 1-substituted-1H-1,2,3,4-tetrazoles by Pd(ii)-polysalophen coated magnetite NPs as a robust versatile nanocomposite
Xu, DaPeng,Xiong, Meilu,Kazemnejadi, Milad
, p. 12484 - 12499 (2021)
A new, versatile, and green methodology has been developed for the efficient NaBH4-reduction of nitroarenes as well as the domino/reduction MCR preparation of 1-substituted-1H-1,2,3,4-tetrazoles using Pd(ii)-polysalophen coated magnetite NPs as an efficient heterogeneous magnetically recyclable nanocatalyst. Polysalophen was firstly prepared based on a triazine framework with a high degree of polymerization, then coordinated to Pd ions and, finally, the resulting hybrid was immobilized on magnetite NPs. The catalyst was characterized by various instrumental and analytical methods, including GPC, DLS, N2adsorption-desorption, TGA, VSM, TEM, HRTEM, EDX, XPS, XRD, and ICP analyses. The catalyst possesses dual-functionality including the reduction of nitroarenes and the construction of tetrazole rings all in one stepviaa domino protocol. High to excellent yields were obtained for both nitro reduction and the direct preparation of 1-substituted-1H-1,2,3,4-tetrazoles from nitro compounds. Insight into the mechanism was conducted by XPSin situas well as DLSin situalong with several control experiments. Recyclability of the catalyst was studied for 6 consecutive runs along with metal leaching measurements in each cycle.
Synthesis of In2S3-CNT nanocomposites for selective reduction under visible light
Yang, Min-Quan,Weng, Bo,Xu, Yi-Jun
, p. 1710 - 1720 (2014)
In2S3-carbon nanotube (In2S 3-CNT) nanocomposites have been prepared via a facile refluxing wet chemistry process. The as-synthesized In2S3-CNT nanocomposites can be used as selective and a
Synthesis, characterization, and application of easily accessible resin-encapsulated nickel nanocatalyst for efficient reduction of functionalized nitroarenes under mild conditions
Rani, Poonam,Singh, Kamal Nain,Kaur, Amarjit
, (2018)
Abstract: A novel resin-encapsulated nickel nanocatalyst has been synthesized by a modified impregnation method using nickel acetate tetrahydrate in presence of sodium borohydride as a mild reducing agent. The synthesized nanocatalyst was characterized by field emission scanning electron microscopy (FESEM) and transmission electron microscopy (TEM). The concentration of nickel nanoparticles encapsulated on resin was determined by inductively coupled plasma-mass spectroscopy (ICP-MS). Further, synthesized resin-encapsulated nickel nanocatalyst was found to be stable and efficient in micromolar concentrations, for the selective reduction of functionalized nitroarenes to corresponding amines in good to high yield, under mild reaction conditions. The nanocatalyst shows excellent reusability. Graphical Abstract: SYNOPSIS A novel resin-encapsulated nickel nanocatalyst (Ni@XAD-4) was synthesized using a modified impregnation method. The nanocatalyst exhibited excellent catalytic activity towards the selective reduction of functionalized nitroarenes in the presence of NaBH 4 with reusability up to five cycles.[Figure not available: see fulltext.].
A convenient and mild synthetic route to aminoarenes by reduction of nitroarenes with activated nickel and hydrazine hydrate
Li, Hongbin,Zhang, Rong,Wang, Hui,Pan, Yi,Shi, Yaozeng
, p. 3047 - 3052 (1997)
Aminoarenes were obtained in excellent yields by reduction of corresponding nitroarenes with activated nickel powder and hydrazine hydrate. The nickel catalyst was prepared by the reduction of anhydrous nickelous chloride with Ultrasonically Dispersed Potassium.
Catalytic application of 1,3,5-triazine-pentaethylenehexamine polymer-supported palladium nanoparticles in the convenient reduction of nitroarenes with sodium borohydride or hydrazine
Gen?, Hayriye,Zengin, Mustafa,Kü?ükislamo?lu, Mustafa,Imamoglu, Mustafa,Toplan, Hüseyin ?zkan,Arslan, Mustafa
, p. 784 - 792 (2017)
The catalytic activity of 1,3,5-triazine-pentaethylenehexamine (TAPEHA) polymer-supported Pd nanoparticles was investigated in the reduction of nitro arenes to the corresponding amines by NaBH4 or N2H4 .H2 O. Optimized reaction conditions for both systems were successfully tested on 20 nitroarenes with different characteristics. Considerably high yields (80%-98% in NaBH4 and 85%-98% in N2H4) were obtained in a short time and at ambient temperature. In addition to these methods being selective against other reducible functionalities such as -CN, -Br, -Cl, and -I, the catalyst can be recovered easily and reused more than ten times.
Efficient reductions of various nitroarenes with scrap automobile catalyst and NaBH4
Genc, Hayriye
, p. 64 - 67 (2015)
The effect of scrap automobile catalyst (SAC), a waste material, was investigated as a catalyst for the reduction of nitroarenes to the corresponding amines with sodium borohydride in aqueous ethanol at 5-25 °C. Along with the observed high conversions, the SAC and NaBH4 combination also exhibits a selectively catalyzed reduction in compounds containing other reducible functionalities, such as CN, Br, Cl and I. Recycling automobile wastes into a catalyst for organic reactions will offer both environmental protection and economic advantages. As a result, an effective, easy to use, low-priced and reliable method has been developed.
CuIBiOI is an efficient novel catalyst in Ullmann-type CN– couplings with wide scope—A rare non-photocatalyic application
Djerdj, Igor,Kónya, Zoltán,Kocsis, Marianna,Kukovecz, ákos,Pálinkó, István,Sipos, Pál,Varga, Gábor
, (2020)
Preparation of a new, mixed-cationic layered CuIBiOI was prepared and its non-photocatalytic catalytic properties were explored. This solid substance had BiOI-like, lamellar and deflected structure resulting from CuI ion incorporation in the Bi2O2 layers. The as-prepared substance was fully characterized by XRD, Raman, far IR, UV–DR, XP spectroscopies, thermal (TG-DTG) and analytical (ICP-MS, SEM-EDX) methods, electron microscopies (SEM, TEM) as well as BET surface area measurements. By performing Ullmann-type CN– coupling reactions between aryl halides and aqueous ammonia, its catalytic capabilities were tested. The effects of solvents, added base and catalyst loading as well as reaction time and reaction temperature were scrutinized, and a green way for the reaction was identified. The recyclability of the catalyst without the loss of activity and its general applicability for a wide range of aryl halides were also demonstrated.
Chemoselective transfer hydrogenation reactions over calcined-layered double hydroxides
Jyothi,Talawar,Raja,Sreekumar,Rajagopal,Rao
, p. 1425 - 1427 (2000)
Layered double hydroxides (LDH) of the hydrotalcite type (also known as anionic clays) could be utilized as precursors of mixed metal oxides with pronounced basic properties. Upon calcination in air at ~ 723 K, these materials give rise to solid solutions between M2+ and M3+ ions (Mg2+, Mn2+, Co2+, Ni2+, Cu2+, Zn2+, and Al3+, Fe3+, Cr3+, respectively). The function of such materials was studied in the reduction of nitrobenzene to aniline using isopropanol as a hydrogen donor, and in the hydrogen-transfer reduction of p-chloronitrobenzene, p-nitroanisole, o-nitrotoluene, m-dinitrobenzene, acetophenone, benzophenone, p-nitroacetophenone, p-nitrobenzophenone, and cinnamaldehyde. The NiII-AlIII (mole ratio = 3:1) catalyst was very active in bringing about chemoselective reduction compared to other calcined LDH.
Preparation, surface and crystal structure, band energetics, optoelectronic, and photocatalytic properties of AuxCd1-xS nanorods
Singh, Rohit,Pal, Bonamali
, p. 851 - 858 (2015)
A series of novel AuxCd1-xS materials (x=0, 0.01, 0.02, 0.03, 0.05, 0.07, 0.1) were prepared and their optical properties, structural-surface morphology, and photocatalytic activity for oxidation and reduction reactions under visible-light irradiation were studied. X-ray diffraction confirmed the shrinkage of the hexagonal crystal structure of CdS; the lattice parameters decreased as a=4.190→4.072 ? and b=c=6.790→6.635 ? with increased loading (1-10 mol%) of the Au3+ dopant. Optical spectra of AuxCd1-xS revealed a significant red-shift (485→538 nm) of the absorption onset and band edge emission (506→530 nm) with notable quenching in photoluminescence. The bandgap energy decreases (2.71→2.41 eV) with increasing Au3+ doping of the CdS nanorods along with considerable shifting of valence band (+1.13→+1.04 eV) and conduction band positions (-1.58→-1.36 eV) versus NHE. The surface area of bare CdS (90.56 m2 g-1) is gradually reduced to 12.32 m2 g-1 with increasing Au3+ doping content. The photocatalytic activity considerably improves with doping, where the Au0.1Cd0.9S composite displays the highest levels of photooxidation (95%) of 0.5 mM salicyldehyde and reduction of 5 mM m-dinitrobenzene to m-nitroaniline (44 %) and m-phenylenediamine (52 %) relative to bare CdS (50 %) probably due to the homogeneous dispersion of Au3+ ions throughout CdS crystal, their superior band-energetics for facile charge-separation and better photostability.
Preparation of carbon supported CuPd nanoparticles as novel heterogeneous catalysts for the reduction of nitroarenes and the phosphine-free Suzuki-Miyaura coupling reaction
Nasrollahzadeh, Mahmoud,Jaleh, Babak,Ehsani, Ali
, p. 1148 - 1153 (2015)
This paper reports on the synthesis and use of CuPd nanoparticles supported on carbon, as highly active catalysts for the reduction of nitroarenes and Suzuki-Miyaura coupling reactions. The catalyst was characterized using the powder XRD, SEM, ICP-AES and EDS techniques. This method has the advantages of high yields, elimination of homogeneous catalysts, simple methodology and easy work up. Catalytic efficiency remains unaltered even after several repeated cycles.
Excellent catalytic properties over nanocomposite catalysts for selective hydrogenation of halonitrobenzenes
Liang, Minghui,Wang, Xiaodong,Liu, Hongquan,Liu, Haichao,Wang, Yuan
, p. 335 - 342 (2008)
A partially reduced Pt/γ-Fe2O3 magnetic nanocomposite catalyst (Pt/γ-Fe2O3-PR) exhibited excellent catalytic properties in the selective hydrogenation of 2, 4-dinitrochlorobenzene and iodonitrobenzenes. The selectivity to 4-chloro-m-phenylenediamine (4-CPDA), meta-iodoaniline (m-IAN), and para-iodoaniline (p-IAN) reached 99.9%, 99.8%, and 99.4%, respectively, at complete conversion of the substrates. The hydrodehalogenation of 4-CPDA and IANs was fully suppressed for the first time over Pt/γ-Fe2O3-PR. It was found that CO chemisorption on the Pt nanoparticles deposited on the partially reduced γ-Fe2O3 and Fe3O4 nanoparticles was very weak, implying a weak tendency of the electronic back-donation from the Pt nanoparticles to the π* antibonding orbitals of the adsorbed molecules. We believe that this is a cause of the superior selectivity to the haloanilines in the hydrogenation reactions of interest over the Pt/γ-Fe2O3-PR catalyst.
METHOD FOR PRODUCING AMINO AROMATIC COMPOUND
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Paragraph 0040-0045, (2021/03/03)
To provide a novel method for producing an amino aromatic compound.SOLUTION: A method for producing a compound (B) having at least one amino group on an aromatic ring, includes at least a step in which a compound (A) at least having an aromatic ring and one group represented by -CR=CH2 [R is a hydrogen atom or a C1-3 alkyl group] on the aromatic ring is reacted with sodium azide in the presence of acid.SELECTED DRAWING: None
Magnetically‐recoverable Schiff base complex of Pd(II) immobilized on Fe3O4@SiO2 nanoparticles: an efficient catalyst for the reduction of aromatic nitro compounds to aniline derivatives
Azadi, Sedigheh,Esmaeilpour, Mohsen,Sardarian, Ali Reza
, p. 809 - 821 (2021/07/20)
Fe3O4@SiO2/Schiff base/Pd(II) is reported as a magnetically recoverable heterogeneous catalyst for the chemoselective reduction of aromatic nitro compounds to the corresponding amines through catalytic transfer hydrogenation (CTH). In this regard, a small amount of the nanocatalyst (0.52?mol% Pd) and hydrazine hydrate, showing safe characteristics and perfect ability as the hydrogen donor, were added to the nitro substrates. The experiments described the successful reduction of aromatic nitro compounds with good to excellent yields and short reaction times. The catalyst, due to its magnetic property, could be simply separated from the reaction mixture by a permanent magnet and reused in seven consecutive reactions without considerable loss in its activity. Moreover, the leaching of Pd was only 3.6% after the seventh run. Thus, the most striking feature of this method is to use a small amount of the magnetic nanocatalyst along with a cheap and safe hydrogen source to produce the important amine substances selectively, which makes the method economical, cheap, environmentally friendly, and simple. Graphic abstract: [Figure not available: see fulltext.]