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

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• 作者：Yue Hu ; Dr. Yinjun Xie ; Zhiqiang Shen and Prof. Dr. Hanmin Huang
• 刊名：Angewandte Chemie International Edition
• 出版年：2017
• 出版时间：February 20, 2017
• 年：2017
• 卷：56
• 期：9
• 页码：2473-2477
• 全文大小：796K
• ISSN：1521-3773

文摘

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 β-hydride elimination of the key Csp³−Pd species was controlled by the confined conformation and the nucleophilicity of the Csp³−Pd bond was enhanced by the strong electron-donating effect of the nitrogen atom.