1030-22-4Relevant articles and documents
Convergent Paired Electrochemical Synthesis of Azoxy and Azo Compounds: An Insight into the Reaction Mechanism
Sadatnabi, Ali,Mohamadighader, Niloofar,Nematollahi, Davood
, p. 6488 - 6493 (2021)
A convergent paired electrochemical method was developed for the synthesis of azoxy and azo compounds starting from the corresponding nitroarenes. We propose a unique mechanism for electrosynthesis of azoxy and azo compounds. We find that both anodic and cathodic reactions are responsible for the synthesis of these compounds. The synthesis of azoxy and azo derivatives have been successfully performed in an undivided cell, using carbon rod electrodes, by constant current electrolysis at room temperature.
Aqueous manganese-mediated reductive coupling of nitroarenes to azoxybenzenes
Dutta, Dilip K.
, p. 1903 - 1906 (2006)
Azoxy compounds have been prepared in good yields by reductive coupling of aromatic nitro compounds with manganese and a catalytic amount of acetic acid in aqueous conditions. Copyright Taylor & Francis Group, LLC.
Tandem selective reduction of nitroarenes catalyzed by palladium nanoclusters
Yan, Ziqiang,Xie, Xiaoyu,Song, Qun,Ma, Fulei,Sui, Xinyu,Huo, Ziyu,Ma, Mingming
, p. 1301 - 1307 (2020)
We report a catalytic tandem reduction of nitroarenes by sodium borohydride (NaBH4) in aqueous solution under ambient conditions, which can selectively produce five categories of nitrogen-containing compounds: anilines, N-aryl hydroxylamines, azoxy-, azo- and hydrazo-compounds. The catalyst is in situ-generated ultrasmall palladium nanoclusters (Pd NCs, diameter of 1.3 ± 0.3 nm) from the reduction of Pd(OAc)2 by NaBH4. These highly active Pd NCs are stabilized by surface-coordinated nitroarenes, which inhibit the further growth and aggregation of Pd NCs. By controlling the concentration of Pd(OAc)2 (0.1-0.5 mol% of nitroarene) and NaBH4, the water/ethanol solvent ratio and the tandem reaction sequence, each of the five categories of N-containing compounds can be obtained with excellent yields (up to 98%) in less than 30 min at room temperature. This tunable catalytic tandem reaction works efficiently with a broad range of nitroarene substrates and offers a green and sustainable method for the rapid and large-scale production of valuable N-containing chemicals.
Stabilisation of gold nanoparticles by N-heterocyclic thiones
Moraes, Leonardo C.,Lacroix, Bertrand,Figueiredo, Rute C.,Lara, Patricia,Rojo, Javier,Conejero, Salvador
, p. 8367 - 8371 (2017)
Gold nanoparticles (Au-NPs) have been prepared using N-heterocyclic thiones (NHTs) as ligand stabilisers. These Au-NPs have been shown to be very stable, even in air, and have been characterized by a combination of several techniques (TEM, HR-TEM, STEM-HAADF, EDX, DLS, elemental analysis and 1H NMR). These nanoparticles are active in the catalytic reduction of nitroarenes to anilines.
Continuous Flow Synthesis of Azoxybenzenes by Reductive Dimerization of Nitrosobenzenes with Gel-Bound Catalysts
Schmiegel, Carsten J.,Berg, Patrik,Obst, Franziska,Schoch, Roland,Appelhans, Dietmar,Kuckling, Dirk
, p. 1628 - 1636 (2021/03/15)
In the search for a new synthetic pathway for azoxybenzenes with different substitution patterns, an approach using a microfluidic reactor with gel-bound proline organocatalysts under continuous flow is presented. Herein the formation of differently substituted azoxybezenes by reductive dimerization of nitrosobenzenes within minutes at mild conditions in good to almost quantitative yields is described. The conversion within the microfluidic reactor is analyzed and used for optimizing and validating different parameters. The effects of the different functionalities on conversion, yield, and reaction times are analyzed in detail by NMR. The applicability of this reductive dimerization is demonstrated for a wide range of differently substituted nitrosobenzenes. The effects of these different functionalities on the structure of the obtained azoxyarenes are analyzed in detail by NMR and single-crystal X-ray diffraction. Based on these results, the turnover number and the turnover frequency were determined.
Selective Photoinduced Reduction of Nitroarenes to N-Arylhydroxylamines
Kallitsakis, Michael G.,Ioannou, Dimitris I.,Terzidis, Michael A.,Kostakis, George E.,Lykakis, Ioannis N.
supporting information, p. 4339 - 4343 (2020/06/08)
We report the selective photoinduced reduction of nitroarenes to N-arylhydroxylamines. The present methodology facilitates this transformation in the absence of catalyst or additives and uses only light and methylhydrazine. This noncatalytic photoinduced transformation proceeds with a broad scope, excellent functional-group tolerance, and high yields. The potential of this protocol reflects on the selective and straightforward conversion of two general antibiotics, azomycin and chloramphenicol, to the bioactive hydroxylamine species.
Preparation of azoxy benzene (by machine translation)
-
Paragraph 0029; 0031, (2020/05/21)
[A] good workability and safety, cost, and, efficient production of the azoxy benzene azoxy benzene can be produced. [Solution] nitrobenzene ones, having the photocatalytic function with a dye, a reducing agent such as a fluorine resin or a transparent resin material is a mixed solution of 1 mm in diameter are inserted into the tube 4 does not inhibit the reaction, 4 LED lamp 5 emits visible from the outside of the tube moves within the tube 4 is provided with visible light within the tube 4 by a photocatalyst reaction mixed solution so as to obtain azoxy benzene compounds. Figure 2 [drawing] (by machine translation)
Synthesis of Azoxybenzenes by Reductive Dimerization of Nitrosobenzene
Chen, Yu-Feng,Chen, Jing,Lin, Li-Jen,Chuang, Gary Jing
, p. 11626 - 11630 (2017/11/10)
Herein we report an effective and simple preparation method of substituted azoxybenzenes by reductive dimerization of nitrosobenzenes. This procedure requires no additional catalyst/reagent and can be applied to substrates with a wide range of substitution patterns.
Mild and selective catalytic oxidation of organic substrates by a carbon nanotube-rhodium nanohybrid
Donck, Simon,Gravel, Edmond,Li, Alex,Prakash, Praveen,Shah, Nimesh,Leroy, Jocelyne,Li, Haiyan,Namboothiri, Irishi N. N.,Doris, Eric
, p. 4542 - 4546 (2015/09/01)
A heterogeneous catalyst was assembled by stabilization of rhodium nanoparticles on carbon nanotubes. The nanohybrid was used for the catalytic aerobic oxidation of diverse substrates such as hydroquinones, hydroxylamines, silanes, hydrazines and thiols, at room temperature. The system proved very efficient on the investigated substrates and demonstrated high selectivity.
Mild, selective and switchable transfer reduction of nitroarenes catalyzed by supported gold nanoparticles
Liu, Xiang,Ye, Sen,Li, Hai-Qian,Liu, Yong-Mei,Cao, Yong,Fan, Kang-Nian
, p. 3200 - 3206 (2013/12/04)
A highly versatile and flexible gold-based catalytic system has been developed for the controlled and selective transfer reduction of nitroarene using 2-propanol as a convenient hydrogen source under mild conditions. Depending on the specific reaction conditions, multiple products including azoxyarenes, symmetric or asymmetric azoarenes and anilines can be obtained respectively via a controlled reduction of the nitro aromatics with good to excellent yields in the presence of a reusable mesostructured ceria-supported gold (Au/meso-CeO2) catalyst. The overall operational simplicity, high chemoselectivity, functional-group tolerance and reusability of the catalyst make this approach an attractive and reliable tool for organic and process chemists. The Royal Society of Chemistry.
