98355-36-3Relevant academic research and scientific papers
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.
STUDIES ON THE MECHANISM OF THE OXIDATION OF AROMATIC PRIMARY AMINES WITH LEAD TETRAACETATE
Benedini, Francesca,Galliani, Guido,Nali, Micaela,Rindone, Bruno,Tollari, Stefano
, p. 343 - 346 (2007/10/02)
The oxidation of eight substituted anilines with lead tetraacetate gives azo derivatives and products deriving from nucleophilic nuclear attack.A ligand transfer mechanism and a reaction path via aminium radical is suggested for these oxidations.
