大学化学 >> 2025, Vol. 40 >> Issue (2): 371-377.doi: 10.12461/PKU.DXHX202405187

所属专题: 自由基化学

化学实验 上一篇    下一篇

可见光催化合成二氟甲基化咖啡因

朱丛军, 张师杰, 郭涛, 袁金伟   

  1. 河南工业大学化学化工学院, 郑州 450001
  • 收稿日期:2024-05-29 录用日期:2024-08-09 发布日期:2025-02-22
  • 通讯作者: 朱丛军, 郭涛, 袁金伟 E-mail:CongjunZhu@haut.edu.cn;taoguo@haut.edu.cn;yuanjinweigs@126.com
  • 基金资助:
    河南工业大学青年骨干教师培育计划;河南省本科高校“化学专业核心课程思政教学团队”项目;河南工业大学化学化工学院教育教学改革研究与实践项目

Visible Light-Catalyzed Synthesis of Difluoromethylated Caffeine

Congjun Zhu, Shijie Zhang, Tao Guo, Jinwei Yuan   

  1. School of Chemistry and Chemical Engineering, Henan University of Technology, Zhengzhou 450001, China
  • Received:2024-05-29 Accepted:2024-08-09 Published:2025-02-22
  • Contact: Congjun Zhu, Tao Guo, Jinwei Yuan E-mail:CongjunZhu@haut.edu.cn;taoguo@haut.edu.cn;yuanjinweigs@126.com

摘要: 可见光催化的反应具有条件温和、反应高效、能耗低、官能团兼容度好等优点,成为了合成化学的有力工具。氮杂环骨架和含氟官能团广泛存在并应用于活性分子中,选择性地将二氟甲基(CF2H)引入到氮杂骨架中有可能显著改变先导候选药物的药理和药代动力学性质。本文报道了在可见光催化下利用双二氟乙酰氧基碘苯作为二氟甲基化试剂,完成了咖啡因的自由基二氟甲基官能团化反应。该反应不涉及过渡金属以及氧化剂,操作简单,易于学生掌握,具有重要的教学及应用价值。

关键词: 可见光催化, 咖啡因, 自由基反应, 二氟甲基化

Abstract: Visible light catalysis offers several advantages, including mild reaction conditions, high efficiency, low energy consumption, and broad functional group compatibility, making it a powerful tool in synthetic chemistry. Nitrogen-containing heterocyclic frameworks and fluorinated functional groups are widely present in bioactive molecules. Selectively introducing a difluoromethyl group (CF2H) into nitrogen heterocycles can significantly influence the pharmacological and pharmacokinetic properties of lead drug candidates. This paper reports a visible light-mediated radical difluoromethylation of caffeine, employing [bis(difluoroacetoxy)iodo]benzene as the difluoromethylating reagent. The reaction proceeds without the need for transition metals or oxidants, is straightforward to perform, and easy for students to learn, offering both educational and practical value.

Key words: Visible light catalysis, Caffeine, Radical reaction, Difluoromethylation