大学化学 >> 2024, Vol. 39 >> Issue (5): 209-217.doi: 10.3866/PKU.DXHX202311024

所属专题： 第4届全国大学生化学实验创新设计大赛

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钯-手性磷酸接力催化的一锅三步串联反应合成手性四氢喹啉

梁仁校1, 钟哲1, 金张灵1, 史丽娟1, 贾义霞1,2   

  1. 1 浙江工业大学化工学院, 杭州 310014;
    2 天津理工大学化学化工学院, 天津 300384
  • 收稿日期:2023-11-06 修回日期:2024-01-05 发布日期:2024-05-25
  • 通讯作者: 梁仁校, 贾义霞 E-mail:liangrx@zjut.edu.cn;yxjia@zjut.edu.cn
  • 基金资助:
    2023年大学生学科竞赛项目(GZ23301010002)

A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline

Renxiao Liang1, Zhe Zhong1, Zhangling Jin1, Lijuan Shi1, Yixia Jia1,2   

  1. 1 College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, China;
    2 School of Chemistry and Chemical Engineering, Tianjin University of Technology, Tianjin 300384, China
  • Received:2023-11-06 Revised:2024-01-05 Published:2024-05-25
  • Contact: Renxiao Liang, Yixia Jia E-mail:liangrx@zjut.edu.cn;yxjia@zjut.edu.cn

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摘要： 设计钯-手性磷酸接力催化体系，以邻碘苯胺和苯基烯丙醇为原料，通过“一锅三步”串联反应高效合成手性2-苯基四氢喹啉，实验无需中间体分离，降低了手性四氢喹啉的合成难度并提高反应经济性，与单一催化反应相比，协同接力催化具有操作简单、反应高效等优点。将协同接力催化的科学前沿引入本科实验教学，融入节能减排和绿色化学等课程思政元素，能拓宽学生的科学视野，激发其学习兴趣并提升创新能力。此外，实验涵盖格氏反应、Heck反应、亚胺缩合反应、不对称氢转移反应等理论知识以及薄层色谱、柱层析色谱、旋转蒸发仪、核磁共振仪、高效液相色谱仪、旋光仪等分析分离设备的操作使用，能综合提升学生的理论水平、实验技能和科学思维能力，促进科研与教学相融合。

关键词: 接力催化, 串联反应, 不对称合成, 四氢喹啉

Abstract: we establish a relay catalysis strategy utilizing Pd(OAc)2/chiral phosphoric acid catalyst for the efficient synthesis of optically active 2-phenyl tetrahydroquinoline via a one-pot three-step domino reaction of 2-iodoaniline with allylic alcohol, eliminating the need for intermediate isolation. Compared to conventional single catalysis methods, this cooperative relay catalysis offers advantages of simplicity and high efficiency. Introducing scientific frontiers such as cooperative relay catalysis into experimental teaching, along with principles of green chemistry and energy saving, broadens students’ scientific perspectives, ignites their passion for learning, and enhances their innovation capabilities. Furthermore, this experiment encompasses fundamental theoretical knowledge including Grignard reactions, Heck reactions, imine condensations, and asymmetric hydrogen transfers, alongside practical analytical techniques such as thin-layer chromatography (TLC), column chromatography, nuclear magnetic resonance (NMR), rotary evaporation, high-performance liquid chromatography (HPLC), and polarimetry. Through this comprehensive experiment, students’ theoretical understanding, experimental skills, and scientific reasoning abilities are enriched, fostering the integration of scientific research and teaching.

Key words: Relay catalysis, Domino reaction, Asymmetric synthesis, Tetrahydroquinoline