352638-79-0Relevant articles and documents
Silver(I)-Catalyzed C-X, C-C, C-N, and C-O Cross-Couplings Using Aminoquinoline Directing Group via Elusive Aryl-Ag(III) Species
Capdevila, Lorena,Andris, Erik,Bri?, Anamarija,Tarrés, Màrius,Roldán-Gómez, Steven,Roithová, Jana,Ribas, Xavi
, p. 10430 - 10436 (2018)
Cross-coupling transformations are a powerful tool in organic synthesis. It is known that this kind of transformation undergoes 2-electron redox processes, and, for this reason, silver has been nearly forgotten as catalyst for cross-couplings because silver is mainly considered as a 1-electron redox metal. Herein, we disclose effective Ag(I)-catalyzed cross-coupling transformations using bidentate aminoquinoline as a directing group toward different nucleophiles to form C-C, C-N, and C-O bonds. DFT calculations indicate the feasible oxidative addition of L1-I substrate via the Ag(I)/Ag(III) catalytic cycle. Furthermore, ion spectroscopy experiments suggest a highly reactive aryl-Ag(III) that in the absence of nucleophiles reacts to form an intermolecular cyclic product [5d-Ag(I)-CH3CN], which in solution forms 5a. This work proves that silver can undergo 2-electron redox processes in cross-coupling reactions like Pd and Cu.
C-5 selective chlorination of 8-aminoquinoline amides using dichloromethane
Lin, Xinxin,Zeng, Cuilian,Liu, Chengkou,Fang, Zheng,Guo, Kai
supporting information, p. 1352 - 1357 (2021/02/26)
An oxidant-free electrochemical regioselective chlorination of 8-aminoquinoline amides at ambient temperature in batch and continuous-flow was achieved. Inert DCM was used as the chlorinating reagent. Owing to the continuous-flow setup, the reaction scale
Regioselective remote C5 cyanoalkoxylation and cyanoalkylation of 8-aminoquinolines with azobisisobutyronitrile
Wen, Chunxia,Zhong, Ronglin,Qin, Zengxin,Zhao, Mengfei,Li, Jizhen
supporting information, p. 9529 - 9532 (2020/09/03)
The efficient regioselective C-H cyanoalkoxylation and cyanoalkylation of 8-aminoquinoline derivatives at the C5 position have been achieved under O2 and N2 atmospheres, respectively. Using 2,2′-azobisisobutyronitrile (AIBN) as a radical precursor, the pr
