15426-16-1Relevant articles and documents
Single crystal MnOOH nanotubes for selective oxidative coupling of anilines to aromatic azo compounds
Cao, Fangxian,Li, Jiayuan,Qu, Yongquan,Zhang, Mingkai,Zhang, Sai,Zou, Yong
supporting information, p. 19692 - 19697 (2021/09/20)
Catalytic synthesis of aromatic azo compounds by oxidative coupling of anilines using molecular oxygen represents a facile, green and valuable process; however, such an economical process suffers from poor catalytic activity and selectivity. Herein, novel single crystal MnOOH nanotubes with abundant Mn3+sites and high oxygen defects were successfully synthesized. The catalyst exhibited high selectivity for oxidative coupling of anilines, achieving complete transformation into aromatic azo compounds under mild conditions, even at room temperature.
Electrosynthesis of Azobenzenes Directly from Nitrobenzenes
Ma, Yanfeng,Wu, Shanghui,Jiang, Shuxin,Xiao, Fuhong,Deng, Guo-Jun
, p. 3334 - 3338 (2021/10/29)
The electrochemical reduction strategy of nitrobenzenes is developed. The chemistry occurs under ambient conditions. The protocol uses inert electrodes and the solvent, DMSO, plays a dual role as a reducing agent. Its synthetic value has been demonstrated by the highly efficient synthesis of symmetric, unsymmetric and cyclic azo compounds.
Convergent Paired Electrochemical Synthesis of Azoxy and Azo Compounds: An Insight into the Reaction Mechanism
Sadatnabi, Ali,Mohamadighader, Niloofar,Nematollahi, Davood
supporting information, p. 6488 - 6493 (2021/08/23)
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.
Conversion of anilines into azobenzenes in acetic acid with perborate and Mo(VI): correlation of reactivities
Karunakaran,Venkataramanan
, p. 375 - 385 (2019/02/14)
Azobenzenes are extensively used to dye textiles and leather and by tuning the substituent in the ring, vivid colours are obtained. Here, we report preparation of a large number of azobenzenes in good yield from commercially available anilines using sodium perborate (SPB) and catalytic amount of Na2MoO4 under mild conditions. Glacial acetic acid is the solvent of choice and the aniline to azobenzene conversion is zero, first and first orders with respect to SPB, Na2MoO4 and aniline, respectively. Based on the kinetic orders, UV–visible spectra and cyclic voltammograms, the conversion mechanism has been suggested. The reaction rates of about 50 anilines at 20–50?°C and their energy and entropy of activation conform to the isokinetic or Exner relationship and compensation effect, respectively. However, the reaction rates, deduced by the so far adopted method, fail to comply with the Hammett correlation. The specific reaction rates of molecular anilines, obtained through a modified calculation, conform to the Hammett relationship. Thus, this work presents a convenient inexpensive non-hazardous method of preparation of a larger number of azobenzenes, and shows the requirement of modification in obtaining the true reaction rates of anilines in acetic acid and the validity of Hammett relationship in the conversion process, indicating operation of a common mechanism.
The palladium and copper contrast: A twist to products of different chemotypes and altered mechanistic pathways
Seth, Kapileswar,Roy, Sudipta Raha,Kumar, Asim,Chakraborti, Asit K.
, p. 2892 - 2896 (2016/05/24)
A novel contrast in palladium and copper catalysis is revealed to form products of different chemotypes resulting in a phenazine to azoarene twist through an altered mechanistic pathway (from non-radical C-H activation mode of C-N coupling to radical N-N coupling) during the oxidative self-coupling of anilines catalysed by Pd-Ag and Cu-Ag nanoclusters.
Bismuth nanoparticles: an efficient catalyst for reductive coupling of nitroarenes to azo-compounds
Pothula, Kishore,Tang, Lin,Zha, Zhenggen,Wang, Zhiyong
, p. 83144 - 83148 (2015/10/19)
The synthesis of azoarenes from corresponding nitroarenes was developed by virtue of in situ bismuth nanoparticles. A series of aromatic azo compounds can be obtained under mild reaction conditions with excellent yields.
Rhenium-Catalyzed [4 + 1] Annulation of Azobenzenes and Aldehydes via Isolable Cyclic Rhenium(I) Complexes
Geng, Xiaoyu,Wang, Congyang
supporting information, p. 2434 - 2437 (2015/05/27)
The first Re-catalyzed [4 + 1] annulation of azobenzenes with aldehydes was developed to furnish 2H-indazoles via isolable and characterized cyclic ReI-complexes. For the first time, the acetate-acceleration effect is showcased in Re-catalyzed C-H activation reactions. Remarkably, mechanistic studies revealed an irreversible aldehyde-insertion step, which is in sharp contrast to those of previous Rh- and Co-systems. (Chemical Presented).
Phenyliodine(III) diacetate (PIDA) mediated synthesis of aromatic azo compounds through oxidative dehydrogenative coupling of anilines: Scope and mechanism
Monir, Kamarul,Ghosh, Monoranjan,Mishra, Subhajit,Majee, Adinath,Hajra, Alakananda
, p. 1096 - 1102 (2014/03/21)
An efficient and environmentally benign method has been developed for the synthesis of symmetrical and unsymmetrical aromatic azo compounds through phenyliodine(III) diacetate (PIDA) mediated oxidative dehydrogenative coupling of anilines in high yields.
Phenyliodine(III) diacetate (PIDA) mediated synthesis of aromatic azo compounds through oxidative dehydrogenative coupling of anilines: Scope and mechanism
Monir, Kamarul,Ghosh, Monoranjan,Mishra, Subhajit,Majee, Adinath,Hajra, Alakananda
, p. 1096 - 1102 (2015/10/05)
An efficient and environmentally benign method has been developed for the synthesis of symmetrical and unsymmetrical aromatic azo compounds through phenyliodine(III) diacetate (PIDA) mediated oxidative dehydrogenative coupling of anilines in high yields.
Highly efficient synthesis of azos catalyzed by the common metal copper (0) through oxidative coupling reactions
Wang, Jiaqing,He, Jing,Zhi, Cong,Luo, Bin,Li, Xinming,Pan, Yue,Cao, Xueqin,Gu, Hongwei
, p. 16607 - 16611 (2014/05/06)
A facile and efficient approach to synthesize symmetric, asymmetric and bridged aromatic azo compounds (AAzos) from aromatic amines was developed by using red copper as catalyst. Despite numerous efforts towards the catalytic synthesis of symmetric and asymmetric AAzos derivatives, most reactions present certain drawbacks inhibiting their industrial applications, such as laborious multi-step processes, harsh reaction conditions and expensive reagents. And the synthesis of bridged azos had low yields before. With the presence of ammonium bromide as co-catalyst, pyridine as a ligand and molecular dioxygen as a sole oxidative reagent, red copper, a common and abundant metal in nature, exhibited unexpected catalytic activity towards the preparation of AAzos in high yields via one-step reaction, making this catalyst an attractive candidate for industrial and synthetic applications.
