19129-74-9Relevant articles and documents
Copper-Manganese Spinel Oxide Catalyzed Synthesis of Amides and Azobenzenes via Aminyl Radical Cations
Sultan, Shaista,Kumar, Manjeet,Devari, Shekaraiah,Mukherjee, Debaraj,Ali Shah, Bhahwal
, p. 703 - 707 (2016)
A highly efficient Cu-Mn-catalyzed process for the aminolysis of esters was developed. Also, the catalyst promoted the self- And cross-dehydrogenative coupling of anilines to generate symmetrical and unsymmetrical azobenzenes, respectively. The reactions were performed under neutral conditions with an inexpensive catalyst, gave high yields, and offered wide functional group tolerance. Spinel tap: A novel facet of aminyl radical cation reactivity with esters for the synthesis of amides is presented. The developed method also gives access to symmetrical and unsymmetrical azobenzenes. The reactions are performed under neutral conditions with an inexpensive catalyst, give high yields, and have a wide functional group tolerance.
Photocatalytic oxidative coupling of arylamines for the synthesis of azoaromatics and the role of O2 in the mechanism
Sitter, James D.,Vannucci, Aaron K.
supporting information, p. 2938 - 2943 (2021/03/01)
The photocatalytic oxidative coupling of aryl amines to selectively synthesize azoaromatic compounds has been realized. Multiple different photocatalysts can be used to perform the general reaction; however, Ir(dF-CF3-ppy)2(dtbpy)+, where dF-CF3-ppy is 2-(2,4-difluorophenyl)-5-(trifluoromethyl)-pyridine and dtpby is 4,4′-tert-butyl-2,2′-bipyridine, showed the greatest range of reactivity with various amine substrates. Both electron-rich and -deficient amines can be coupled with yields up to 95% under an ambient air atmosphere. Oxygen was deemed to be essential for the reaction and is utilized in the regeneration of the photocatalyst. Fluorescence quenching and radical trap experiments indicate an amine radical coupling mechanism that proceeds through a hydrazoaromatic intermediate before further oxidation occurs to form the desired azoaromatic products.
Chemoselective electrochemical reduction of nitroarenes with gaseous ammonia
Chang, Liu,Li, Jin,Wu, Na,Cheng, Xu
supporting information, p. 2468 - 2472 (2021/04/02)
Valuable aromatic nitrogen compounds can be synthesized by reduction of nitroarenes. Herein, we report electrochemical reduction of nitroarenes by a protocol that uses inert graphite felt as electrodes and ammonia as a reductant. Depending on the cell voltage and the solvent, the protocol can be used to obtain aromatic azoxy, azo, and hydrazo compounds, as well as aniline derivatives with high chemoselectivities. The protocol can be readily scaled up to >10 g with no decrease in yield, demonstrating its potential synthetic utility. A stepwise cathodic reduction pathway was proposed to account for the generations of products in turn.
