620-81-5Relevant articles and documents
Visible-light-induced direct construction of amide bond from carboxylic acids with amines in aqueous solution
Wang, Jin,Hou, Huiqing,Hu, Yongzhi,Lin, Jin,Wu, Min,Zheng, Zhiqiang,Xu, Xiuzhi
supporting information, (2021/02/09)
A novel visible-light-promoted N-acylation for the synthesis of amides from easily available carboxylic acids with amines in the presence of I2 within 2.5 h in aqueous solution has been developed. Using sunlight as the visible light source greatly reduces the cost of experiments and produces almost no toxic effects. Hence, this study provides an alternative catalytic system for the construction of a wide range of amides with readily available materials. Moreover, the strategy was successfully applied in the preparation of N-(3-(2,6-dimethoxyphenoxy)-7-nitroquinoxalin-2-yl)benzohydrazide, which displayed a signification anti-proliferation effect on A549, MCF-7 and HCT116 cell lines.
Copper-Catalyzed Ullmann-Type Coupling and Decarboxylation Cascade of Arylhalides with Malonates to Access α-Aryl Esters
Chen, Fen-Er,Chen, Tao,Cheng, Fei,Huang, Yin-Qiu,Li, Jia-Wei,Xiao, Xiao,Zhou, Chen
, (2022/01/04)
We have developed a high-efficiency and practical Cu-catalyzed cross-coupling to directly construct versatile α-aryl-esters by utilizing readily available aryl bromides (or chlorides) and malonates. These gram-scale approaches occur with turnovers of up to 1560 and are smoothly conducted by the usage of a low catalyst loading, a new available ligand, and a green solvent. A variety of functional groups are tolerated, and the application occurs with α-aryl-esters to access nonsteroidal anti-inflammatory drugs (NSAIDs) on the gram scale.
Theoretical and Experimental Studies: Cu(I)/Cu(II) Catalytic Cycle in CuI/Oxalamide-Promoted C-N Bond Formation
Morarji, Devita V.,Gurjar, Kamlesh K.
supporting information, (2019/07/03)
In modern Ullmann-Goldberg reactions, cheaper aryl chlorides are poor substrates. Recently, attention has been paid to facile CuI/oxalamide-promoted arylation of heteroatoms (N, O, and S) using cheaper aryl chlorides. However, the mechanism of the reaction and the role of oxalamides have not yet been investigated. In the present investigation, theoretical (density functional theory) and supporting in situ 1H NMR spectroscopy, UV-vis spectroscopy, Fourier transform infrared spectroscopy, and cyclic voltammetry studies have been performed to provide insight into the various aspects of the mechanism. Five different possible pathways have been investigated. [LCu(NHNu)] is the active copper catalytic species, in which L (oxalamide) coordinates Cu(I) through both C=O groups. Our studies show that the reaction follows an outer-sphere single-electron transfer pathway. Moreover, these studies also address the reason for the deactivation of a copper catalyst.
