Palladium-Catalyzed Ring-Forming Aminoalkenylation of Alkenes with Aldehydes Initiated by Intramolecular Aminopalladation

被引:20
作者
Hu, Yue [1 ,3 ]
Xie, Yinjun [1 ]
Shen, Zhiqiang [1 ]
Huang, Hanmin [1 ,2 ]
机构
[1] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China
[2] Univ Sci & Technol China, Dept Chem, Hefei 230026, Peoples R China
[3] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
基金
中国国家自然科学基金;
关键词
aminopalladation; beta-hydride elimination; nucleophilic addition; palladium; tandem reactions; C-H BONDS; AEROBIC OXIDATIVE AMINATION; CROSS-COUPLING REACTIONS; N-FLUOROBENZENESULFONIMIDE; CIS-AMINOPALLADATION; ARYLBORONIC ACIDS; DIRECT ADDITION; ALKYNES; FUNCTIONALIZATION; CYCLIZATION;
D O I
10.1002/anie.201611853
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A palladium-catalyzed aminopalladation reaction followed by nucleophilic addition with aldehydes and dehydration is described. This direct and operationally simple procedure provides a rapid and reliable approach to a wide range of functionalized tetrahydroisoquinolines with high selectivity. Mechanistic studies disclosed that the nucleophilic addition, performed via a highly ordered transition-state, is the turnover-limiting step in which the inherent beta-hydride elimination of the key Csp(3)-Pd species was controlled by the confined conformation and the nucleophilicity of the Csp(3)-Pd bond was enhanced by the strong electron-donating effect of the nitrogen atom.
引用
收藏
页码:2473 / 2477
页数:5
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