绿色化学导向的[4+1]环加成反应创新化学实验设计

曲宝乐; 陆良秋

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曲宝乐,陆良秋.化学通报,2025,88(11):1236-1241.

绿色化学导向的[4+1]环加成反应创新化学实验设计

An Innovative Chemistry Experiment Design on Green Chemistry-Oriented [4+1] Cycloaddition Reaction

投稿时间：2025-06-13 修订日期：2025-07-08

DOI：

中文关键词: 绿色合成可见光铜催化硫叶立德

英文关键词:Green synthesis, Visible light, Copper catalysis, Sulfur ylide

基金项目:国家自然科学基金项目(22471089和22271113)和中央高校基本科研业务费项目(30106190336)资助

作者	单位	E-mail
曲宝乐	华中师范大学化学学院	baolequ@mails.ccnu.edu.cn
陆良秋^*	华中师范大学化学学院	luliangqiu@ccnu.edu.cn

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中文摘要:

可见光诱导反应与廉价金属催化是绿色合成的两个重要策略,其教学转化对推动化学实验教学改革具有重要意义。本研究基于“科研反哺教学”理念,开发了可见光诱导与铜催化协同的硫叶立德[4+1]环加成教学实验。该反应通过光诱导卡宾转移原位生成硫叶立德,高效构建吲哚啉骨架(收率82%),体现了绿色合成的协同优势。实验涵盖无水无氧操作、TLC监测、柱层析纯化及HRMS/NMR表征等核心技能,强化了学生对光化学与铜催化机制的理解,并为前沿科研成果向教学转化提供了实践范例。

英文摘要:

Visible-light-induced reactions and base-metal catalysis are two important strategies in green synthesis. Integrating these strategies into teaching is highly significant for advancing chemical education reform. Guided by the "research-to-teaching" philosophy, this study developed a teaching experiment based on a visible-light-induced/copper-catalyzed [4+1] cycloaddition employing sulfur ylides. This reaction efficiently constructs indoline scaffolds with an 82% yield through photoinduced carbene transfer, generating sulfur ylides in situ and demonstrating the synergistic benefits of green synthesis. The experimental procedure incorporates key techniques, such as Schlenk operations, thin-layer chromatography (TLC) monitoring, flash column chromatography, and high-resolution mass spectrometry (HRMS) and nuclear magnetic resonance (NMR) characterization. These techniques effectively enhance students" understanding of photochemical and copper-catalyzed processes. This work provides a practical model for translating cutting-edge research findings into educational applications.

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