135033-23-7Relevant academic research and scientific papers
Photoinduced Coupling Reaction of Benzotriazole with Aromatic Hydrocarbons Sensitized by 9,10-Dicyanoanthracene (DCA) via an Electron-transfer Mechanism. A Simple Synthesis of 1-Arylbenzotriazole
Xu, Jianhua,He, Jinping,Qian, Yue
, p. 714 - 715 (1991)
The photoinduced coupling reaction of benzotriazole with aromatic hydrocarbons (anisole, biphenyl and naphthalene) is sensitized by 9,10-dicyanoanthracene (DCA) to give 1-arylbenzotriazoles in moderate yields via an electron-transfer mechanism.
The Disappearing Director: The Case of Directed N-Arylation via a Removable Hydroxyl Group
Andrzejewska, Magdalena R.,Vuram, Prasanna K.,Pottabathini, Narender,Gurram, Venkateshwarlu,Relangi, Siva Subrahmanyam,Korvinson, Kirill A.,Doddipalla, Raju,Stahl, Lothar,Neary, Michelle C.,Pradhan, Padmanava,Sharma, Somesh,Lakshman, Mahesh K.
supporting information, p. 2503 - 2510 (2018/05/08)
A facile and broadly applicable method for the regiospecific N-arylation of benzotriazoles is reported. Copper-mediated reactions of diverse 1-hydroxy-1H-benzotriazoles with aryl boronic acids lead to 1-aryl-1H-benzotriazole 3-oxides. A N1-OH→N3 prototropy in the 1-hydroxy-1H-benzotriazoles is plausibly the underlying basis, where the tautomer is captured by the boronic acid, leading to C?N (not C?O) bond formation. Because the N?O bond in amine N-oxides and 1-hydroxy-1H-benzotriazoles can be easily reduced by diboron reagents such as (pinB)2 and B2(OH)4, exposure of the 1-aryl-1H-benzotriazole 3-oxides to B2(OH)4 then leads to facile reduction of the N?O bond resulting in diverse, regiospecifically-arylated benzotriazoles. Thus, the N-hydroxyl group in 1-hydroxy-1H-benzotriazoles acts as a disposable arylation director. (Figure presented.).
