1227476-15-4Relevant articles and documents
Ethylenediamine promoted the hydrogenative coupling of nitroarenes over Ni/C catalyst
Yang, Youdi,Li, Shaopeng,Xie, Chao,Liu, Hangyu,Wang, Yanyan,Mei, Qingqing,Liu, Huizhen,Han, Buxing
, p. 203 - 206 (2019)
Azobenzene and its derivatives are key raw materials and it is an environmentally friendly method for the preparation of azobenzene by hydrogenative coupling of nitrobenzene. The development of nickel based catalyst for organic transformations is of importance because of its relatively low cost and toxicity. In this work, we found that ethylenediamine can enrich the electron state of Ni and make the azobenzene easily desorb from the surface of the catalyst, which inhibits the hydrogenation of azobenzene to aniline. The selectivity of azobenzene is greatly improved. When the ratio of Ni and ethylenediamine is 1:10, the yield of the azobenzene can reach 95.5%.
Catalytic nickel nanoparticles embedded in a mesoporous metal-organic framework
Park, Young Kwan,Choi, Sang Beom,Nam, Hye Jin,Jung, Duk-Young,Ahn, Hee Choon,Choi, Kihang,Furukawa, Hiroyasu,Kim, Jaheon
, p. 3086 - 3088 (2010)
Ni nanoparticles embedded in the pores of a mesoporous MOF (MesMOF-1) act as a catalyst for hydrogenolysis of nitrobenzene or hydrogenation of styrene. The Royal Society of Chemistry 2010.
Silver and palladium alloy nanoparticle catalysts: Reductive coupling of nitrobenzene through light irradiation
Peiris, Sunari,Sarina, Sarina,Han, Chenhui,Xiao, Qi,Zhu, Huai-Yong
, p. 10665 - 10672 (2017)
Silver-palladium (Ag-Pd) alloy nanoparticles strongly absorb visible light and exhibit significantly higher photocatalytic activity compared to both pure palladium (Pd) and silver (Ag) nanoparticles. Photocatalysts of Ag-Pd alloy nanoparticles on ZrO2 and Al2O3 supports are developed to catalyze the nitroaromatic coupling to the corresponding azo compounds under visible light irradiation. Ag-Pd alloy NP/ZrO2 exhibited the highest photocatalytic activity for nitrobenzene coupling to azobenzene (yield of ～80% in 3 hours). The photocatalytic efficiency could be optimized by altering the Ag:Pd ratio of the alloy nanoparticles, irradiation light intensity, temperature and wavelength. The rate of the reaction depends on the population and energy of the excited electrons, which can be improved by increasing the light intensity or by using a shorter wavelength. The knowledge developed in this study may inspire further studies on Ag alloy photocatalysts and organic syntheses using Ag-Pd nanoparticle catalysts driven under visible light Irradiation.
A NOVEL REACTION OF ACETANILIDE WITH NITROBENZENE IN DMSO - AN UNUSUAL SOLVENT ASSISTED REGIOSELECTIVE AROMATIC NUCLEOPHILIC SUBSTITUTION
Ayyangar, N. R.,Naik, S. N.,Srinivasan, K. V.
, p. 3217 - 3220 (1990)
The reaction of acetanilide (1) with nitrobenzene (2) in the presence of a base in DMSO yielded p-nitrosodiphenylamine (3) as the major product.This unusual regioselective formation of the deoxygenated product 3 has been rationalized in terms of solvent effects exerted by DMSO.
Synthesis of azo compounds by nanosized iron-promoted reductive coupling of aromatic nitro compounds
Moglie, Yanina,Vitale, Cristian,Radivoy, Gabriel
, p. 1828 - 1831 (2008)
Treatment of a variety of aromatic nitro compounds with the active-iron based reducing system composed of FeCl2·4H2O, an excess of lithium powder and a catalytic amount of 4,4′-di-tert-butylbiphenyl (DTBB, 5 mol %) in THF at room temperature, led to the formation of the corresponding symmetrically substituted azo compounds in good yield, resulting from a reductive coupling process. Some other functionalities including carbonyl, halogen, amino and hydroxyl groups, demonstrated to be compatible with the reaction conditions, giving none reduced or coupled by-products. In all cases, the azo compounds formed have not experienced over-reduction to the corresponding hydrazo or amino derivatives even upon prolonged heating or using an excess of the reducing system.
A new preparative method, characterization, and reactivity of disulphide dication salts of cyclic bis-sulphides: R2S-SR2· 2CF3SO3-
Fujihara, Hisashi,Akaishi, Ryouichi,Furukawa, Naomichi
, p. 930 - 931 (1987)
The reaction of 1,5-dithiacyclo-octane 1-oxide with trifluoromethanesulphonic anhydride affords the corresponding disulphide dication as a stable crystalline salt which serves as an oxidizing agent in the oxidation of 1,2-diphenylhydrazine; the disulphide dication of 1,4-dithiane has also been isolated.
Synthesis, Structure, and Oxidative Reactivity of a Class of Thiolate-Bridged Dichromium Complexes Featuring Antiferromagnetic Coupling Interactions
Wei, Nianmin,Yang, Dawei,Zhang, Yixin,Wang, Baomin,Qu, Jingping
, p. 923 - 928 (2021)
Several thiolate-bridged dichromium complexes with Cp* (Cp=η5-C5Me5) as auxiliary ligands were designed and synthesized through the salt metathesis, which all contain two six-coordinate chromium centers in the formal valence of +3. These complexes are all paramagnetic species, which are in good agreement with the experimental results that broad and paramagnetically shifted proton resonances appear in the 1H NMR spectra. Furthermore, variable-temperature solid-state magnetic susceptibility studies reveal the two chromium centers of these complexes are both in an S=3/2 high-spin state with a strong antiferromagnetic coupling. Simulated values of antiferromagnetic coupling constant for these complexes are directly related to the distances of the two CrIII centers confirmed by X-ray crystallography. In addition, in the presence of dehalogenation agent AgPF6, complexes [Cp*CrCl(μ-SR)2CrClCp*] (3, R=Et; 4, R=iPr) and [Cp*Cr(μ-Cl)(μ-SEt)2CrCp*][BPh4] (5) containing easily removable chloride can achieve the catalytic oxidation of organic substrates, such as PPh3, 1,4-cyclohexadiene and 1,2-diphenylhydrazine under an oxygen atmosphere.
A new catalytic method for the selective oxidation of aniline to nitrosobenzene over titanium silicate molecular sieves, TS-1, using H2O2 as oxidant
Selvam,Ramaswamy
, p. 1215 - 1216 (1996)
The oxidation of aniline to nitrosobenzene with a selectivity > 73% has been achieved using titanium silicate molecular sieves, TS-1 as catalyst and aqueous H2O2 as oxidant at 273 K in a batch reaction.
Di- and Trinuclear Iridium(III) Complexes with Poly-Mesoionic Carbenes Synthesized through Selective Base-Dependent Metalation
Maity, Ramananda,Van Der Meer, Margarethe,Hohloch, Stephan,Sarkar, Biprajit
, p. 3090 - 3096 (2015)
Mutidentate carbene ligands based on a rigid aromatic platform are valuable synthons for generating carbene complexes with higher nuclearity. We present here the selective, base-dependent synthesis of a dinuclear or a trinuclear IrIII complex from the 1,3,5-substituted benzene derived tris-triazolium salt. The dinuclear IrIII complex features an unreacted triazolium unit which enables us to compare the metric parameters between the bonded 1,2,3-triazol-5-ylidene to their parent triazolium salt present in the same molecule. Single crystal X-ray diffraction studies confirm the di- and trinuclear nature of the complexes and establish their configuration and conformation. Both the di- and trinuclear IrIII complexes have been used for catalytic transfer hydrogenation, and these complexes are potent precatalysts delivering good to excellent yields for the reduction of benzaldehyde, acetophenone, benzophenone, and cyclohexanone. Furthermore, they show a preference for reducing nitrobenzene to either azoxybenzene or azobenzene. Mercury poisoning tests conclusively prove the homogeneous nature of the reported catalysis. The lack of orthometalation in these complexes and the possible effect thereof on catalysis are discussed. (Chemical Equation Presented).
Biogenic Synthesis of Gold Nanoparticles on a Green Support as a Reusable Catalyst for the Hydrogenation of Nitroarene and Quinoline
Adeyeye Nafiu, Sodiq,Aziz, Abdul,Shaheen Shah, Syed,Shaikh, M. Nasiruzzaman
, p. 1956 - 1966 (2021)
Direct attachment of gold nanoparticles to a green support without the use of an external reducing agent and using it for removing toxic pollutants from wastewater, i. e., reduction of nitroarene to amine, are described. A novel approach involving the reduction of gold by the jute plant (Corchorus genus) stem-based (JPS) support itself to form nanoparticles (AuNPs) to be used as a catalytic system (‘dip-catalyst’) and its catalytic activity for the hydrogenation of series of nitroarenes in aqueous media are presented. AuNPs/JPS catalyst was characterized using SEM, UV-Vis, FTIR, TEM, XPS, and ICP-OES. Confined area elemental mapping exhibits uniform and homogeneous distribution of AuNPs on the support surface. TEM shows multi-faceted AuNPs in the range of 20–30 nm. The reactivity of AuNPs/JPS for the transfer hydrogenation of nitroarene as well as hydrogenation of quinoline under molecular H2 pressure was evaluated. Sodium borohydride, when used as the hydrogen source, demonstrates a high catalytic efficiency in the transfer hydrogenation reduction of 4-nitrophenol (4-NP). Quinoline is quantitatively and chemoselectively hydrogenated to 1,2,3,4-tetrahydroquinoline (py-THQ) using molecular hydrogen. Reusability studies show that AuNPs are stable on the support surface and their selectivity is not affected.
