497-87-0Relevant articles and documents
Selective Oxidation of Anilines to Azobenzenes and Azoxybenzenes by a Molecular Mo Oxide Catalyst
Han, Sheng,Cheng, Ying,Liu, Shanshan,Tao, Chaofu,Wang, Aiping,Wei, Wanguo,Yu, Han,Wei, Yongge
supporting information, p. 6382 - 6385 (2021/02/09)
Aromatic azo compounds, which play an important role in pharmaceutical and industrial applications, still face great challenges in synthesis. Herein, we report a molybdenum oxide compound, [N(C4H9)4]2[Mo6O19] (1), catalyzed selective oxidation of anilines with hydrogen peroxide as green oxidant. The oxidation of anilines can be realized in a fully selectively fashion to afford various symmetric/asymmetric azobenzene and azoxybenzene compounds, respectively, by changing additive and solvent, avoiding the use of stoichiometric metal oxidants. Preliminary mechanistic investigations suggest the intermediacy of highly active reactive and elusive Mo imido complexes.
The polyhedral nature of selenium-catalysed reactions: Se(iv) species instead of Se(vi) species make the difference in the on water selenium-mediated oxidation of arylamines
Capperucci, Antonella,Dalia, Camilla,Tanini, Damiano
supporting information, p. 5680 - 5686 (2021/08/16)
Selenium-catalysed oxidations are highly sought after in organic synthesis and biology. Herein, we report our studies on the on water selenium mediated oxidation of anilines. In the presence of diphenyl diselenide or benzeneseleninic acid, anilines react with hydrogen peroxide, providing direct and selective access to nitroarenes. On the other hand, the use of selenium dioxide or sodium selenite leads to azoxyarenes. Careful mechanistic analysis and 77Se NMR studies revealed that only Se(iv) species, such as benzeneperoxyseleninic acid, are the active oxidants involved in the catalytic cycle operating in water and leading to nitroarenes. While other selenium-catalysed oxidations occurring in organic solvents have been recently demonstrated to proceed through Se(vi) key intermediates, the on water oxidation of anilines to nitroarenes does not. These findings shed new light on the multifaceted nature of organoselenium-catalysed transformations and open new directions to exploit selenium-based catalysis.
A Green Chemoenzymatic Process for the Synthesis of Azoxybenzenes
Yang, Fengjuan,Wang, Zhi,Zhang, Xiaowen,Jiang, Liyan,Li, Yazhuo,Wang, Lei
, p. 3450 - 3453 (2015/11/10)
An efficient chemoenzymatic process for the synthesis of azoxybenzenes was developed. A peracid was generated in situ by Novozym 435, and then a range of anilines were oxidized by the produced peracid to afford azoxybenzenes in yields ranging from 63.1 to 94.1 %. This method expands the application of lipase in organic synthesis and provides an alternative method for the synthesis of azoxybenzenes.
