1570075-60-3Relevant academic research and scientific papers
Nickel-Catalyzed Intramolecular Desulfitative C - N Coupling: A Synthesis of Aromatic Amines
Chen, Xuemeng,Jia, Xiuwen,Kramer, S?ren,Li, Yue,Lian, Zhong,Liu, Jiangjun,Sun, Haotian
, p. 5702 - 5711 (2020/05/19)
A nickel-catalyzed intramolecular C - N coupling reaction via SO2 extrusion is presented. The use of a catalytic amount of BPh3 allows the transformation to take place under much milder conditions (60 °C) than previously reported C - N coupling reactions by CO or CO2 extrusion (160-180 °C). In addition, this method displays good functional group tolerance and versatility, as it can be applied to the synthesis of dialkyl aryl amines, alkyl diaryl amines, and triaryl amines. The robustness of the desulfitative C - N coupling is demonstrated by three high-yielding gram-scale reactions.
Palladium(II)-catalyzed direct ortho arylation of 4-methyl-N-phenylpyridin- 2-amines via C-H activation/C-C coupling and synthetic applications
Chu, Jean-Ho,Huang, Hao-Ping,Hsu, Wen-Ting,Chen, Shih-Tien,Wu, Ming-Jung
, p. 1190 - 1204 (2014/04/03)
The direct ortho arylation of 4-methyl-N-phenylpyridin-2-amines via palladium(II)-catalyzed C-H activation is described. Treatment of 4-methyl-N-phenylpyridin-2-amine with potassium aryltrifluoroborate using 10 mol % of palladium(II) acetate as the catalyst, 2 equiv of copper(II) acetate as the oxidant, and 1 equiv of p-benzoquinone in tert-butyl alcohol gave ortho-arylated products in modest to excellent yields. This reaction shows good functional group compatibility. A series of 1H NMR titration experiments and controlled experiments elucidating the reaction mechanism were carried out. The key intermediate, 4-methyl-N-phenylpyridin-2-amine palladacycle, was isolated and characterized by X-ray crystallography. The advanced transformations of ortho-phenylated 4-methyl-N-phenylpyridin-2-amine to N-(4-methylpyridin-2-yl)-9H-carbazole, biphenyl-2-amine, and 3-methyl-6-phenylpyrido[1,2-a]benzimidazole were successfully demonstrated as potential synthetic applications.
