大学化学 >> 2026, Vol. 41 >> Issue (5): 222-229.doi: 10.12461/PKU.DXHX202511044

所属专题： 第5届全国大学生化学实验创新设计大赛

专题 上一篇    

电化学合成4-氯-2-三异丙基硅基喹啉

吴梦云, 邓雨欣, 王文慧, 许冬冬, 谢兰贵, 孙培培   

  1. 南京师范大学化学与材料科学学院, 江苏 南京 210023
  • 收稿日期:2025-11-06 录用日期:2026-02-26 发布日期:2026-05-21
  • 通讯作者: 许冬冬, 谢兰贵, 孙培培 E-mail:07239@njnu.edu.cn;xielg@njnu.edu.cn;sunpeipei@njnu.edu.cn Dongdong Xu, Langui Xie, Peipei Sun
  • 基金资助:
    江苏省化学优势学科项目

Electrochemical synthesis of 4-chloro-2-(triisopropylsilyl) quinoline

Mengyun Wu, Yuxin Deng, Wenhui Wang, Dongdong Xu, Langui Xie, Peipei Sun   

  1. School of Chemistry and Materials Science, Nanjing Normal University, Nanjing 210023, Jiangsu Province, China
  • Received:2025-11-06 Accepted:2026-02-26 Published:2026-05-21
  • Contact: Dongdong Xu, Langui Xie, Peipei Sun E-mail:07239@njnu.edu.cn;xielg@njnu.edu.cn;sunpeipei@njnu.edu.cn

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摘要： 传统有机化学反应途径包含离子反应、协同反应、自由基反应三大类型，当前绝大多数本科生有机化学实验教材主要聚焦前两类，而自由基反应相对缺少，因此需增加相关实验，让同学们对这类反应及条件控制有初步的认识。考虑到有机硅化合物不仅是重要的有机合成原料，还具有多种生物活性，在材料化学领域也有极大的应用价值，本实验设计以4-氯喹啉和三异丙基硅烷为原料，通过电流驱动自由基反应合成硅基取代的杂环化合物4-氯-2-三异丙基硅基喹啉。本实验提供了一个将自由基反应和电化学合成技术应用于本科有机化学实验教学的案例，希望藉此拓宽本科生视野，使其初步认识自由基反应过程，了解更多的现代有机合成方法，培养创新意识，增强对有机化学的兴趣。本实验符合绿色化学理念，具备高效、高原子经济性、产物收率高、重复性良好等优点。

关键词: 自由基反应, 电化学合成, 有机硅化合物, 本科实验教学

Abstract: Conventional organic reaction mechanisms primarily encompass three categories: ionic reactions, concerted reactions, and radical reactions. While current undergraduate organic chemistry laboratory curricula predominantly emphasize the first two types, radical reactions remain notably underrepresented. This pedagogical gap necessitates the inclusion of relevant experimental procedures to facilitate students’ fundamental comprehension of radical reactions and their condition optimization. Given that organosilicon compounds not only serve as crucial synthetic intermediates but also demonstrate diverse biological activities and substantial applications in materials chemistry, this experiment employs 4-chloroquinoline and triisopropylsilane as starting materials to synthesize 4-chloro-2-triisopropylsilylquinoline through an electrochemically mediated radical pathway. Designed for undergraduate chemistry education, this experiment integrates radical chemistry with modern electrochemical synthesis techniques, aiming to broaden students’ perspectives on reaction mechanisms, introduce contemporary synthetic methodologies, foster innovative thinking, and enhance engagement with organic chemistry. The protocol adheres to green chemistry principles, exhibiting superior characteristics including operational efficiency, exceptional atom economy, high product yield, and excellent reproducibility.

Key words: Radical reaction, Electrochemical synthesis, Organosilicon compound, Undergraduate experimental education