大学化学 >> 2024, Vol. 39 >> Issue (12): 235-243.doi: 10.12461/PKU.DXHX202404035

所属专题： 自由基化学

化学实验 上一篇    下一篇

光铜协同催化合成α-甲基4-联苯腈

张斌1, 李甜甜1, 宋易恬1, 程莹1, 陈加荣1,2   

  1. 1 华中师范大学化学学院, 武汉 430079;
    2 化学国家级实验教学示范中心(华中师范大学), 武汉 430079
  • 收稿日期:2024-04-07 录用日期:2024-04-23 发布日期:2024-12-17
  • 通讯作者: 陈加荣 E-mail:chenjiarong@mail.ccnu.edu.cn
  • 基金资助:
    国家自然科学基金面上项目(22171099)

Photoredox and Copper Co-Catalyzed Synthesis of α-Methyl-4-Biphenylacetonitrile

Bin Zhang1, Tiantian Li1, Yitian Song1, Ying Cheng1, Jiarong Chen1,2   

  1. 1 College of Chemistry, Central China Normal University, Wuhan 430079, China;
    2 National Demonstration Center for Experimental Chemistry Education (Central China Normal University), Wuhan 430079, China
  • Received:2024-04-07 Accepted:2024-04-23 Published:2024-12-17
  • Contact: Jiarong Chen E-mail:chenjiarong@mail.ccnu.edu.cn

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摘要： 光-铜协同催化的自由基反应已经在有机合成领域中得到了广泛应用，具有产率高、条件温和、官能团兼容性好以及环境友好等特点。基于绿色可持续发展理念，我们以工业原料烯烃和商业化三甲基氰硅烷以及水为原料，在温和条件下高效合成了高附加值的腈类化合物。本实验综合性高，操作性强，涵盖无水无氧操作、薄层色谱法和快速柱层析操作、气相色谱-质谱联用以及核磁分析等多项实验操作。此外该反应原料易得，条件温和，无需复杂仪器，重现性高，保证学生实验技能得到锻炼，同时也培养了学生的创新能力，让学生了解有机化学的发展前沿，具有重要的应用价值和教学价值。

关键词: 可见光催化, 铜催化, 烯烃转化, 腈类化合物, 有机化学实验

Abstract: The synergistic use of photoredox and copper catalysis in free radical reactions has gained extensive application in organic synthesis due to its high yield, mild reaction conditions, excellent functional group compatibility, and environmental friendliness. In alignment with the principles of green and sustainable development, we have efficiently synthesized high-value nitrile compounds from industrial raw materials, such as olefins, commercially available trimethylcyanosilane, and water under mild conditions using visible light irradiation. This comprehensive experiment encompasses a variety of techniques, including anhydrous and anaerobic operations, thin-layer chromatography (TLC), flash column chromatography, gas chromatography-mass spectrometry (GC-MS), and nuclear magnetic resonance (NMR) analysis. Additionally, the experiment is characterized by easily accessible starting materials, mild reaction conditions, and high reproducibility, eliminating the need for complex instrumentation. This ensures that students can enhance their experimental skills, foster their innovative capabilities, and gain exposure to the forefront of organic chemistry. Hence, this experiment holds significant practical and educational value.

Key words: Visible-light photocatalysis, Copper catalysis, Olefin conversion, Nitrile compounds, Organic chemistry experiment