4953-10-0Relevant articles and documents
Magnetically recoverable copper nanorods and their catalytic activity in Ullmann cross-coupling reaction
Rajabzadeh, Maryam,Eshghi, Hossein,Khalifeh, Reza,Bakavoli, Mehdi
, (2017)
A novel polydentate ligand supported on Fe3O4@SiO2 was designed and demonstrated for the synthesis of Cu nanorods. The Fe3O4@SiO2/EP.EN.EG@Cu was characterized using X-ray diffraction, ther
Cu-catalyzed arylation of 1-acyl-1H-1,2,3-Benzotriazoles via C–N activation
Zhang, Wenying,Wang, Yangyang,Jia, Xiangru,Du, Zhengyin,Fu, Ying
, p. 64 - 67 (2019/06/10)
An efficient copper-catalyzed arylation reaction of 1-acyl-1H-1,2,3-benzotriazoles with diaryliodonium salts via C–N activation is explored. The reaction is conducted regioselectively to form 1-aryl-1H-1,2,3-benzotriazoles in MeCN at 80 °C in the presence of cesium carbonate. 29 examples are given with the product yield of up to 84%. The probable reaction mechanism is proposed.
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.).