大学化学 >> 2025, Vol. 40 >> Issue (6): 238-247.doi: 10.12461/PKU.DXHX202408092

化学实验 上一篇    下一篇

光催化碳氢键官能团化合成1-苯基-1,2-乙二醇

平媛媛1, 孔望清1,2   

  1. 1 武汉大学高等研究院, 武汉 430072;
    2 化学国家级实验教学示范中心(武汉大学), 武汉 430072
  • 收稿日期:2024-08-24 录用日期:2024-10-14 发布日期:2025-06-20
  • 通讯作者: 孔望清 E-mail:wqkong@whu.edu.cn
  • 基金资助:
    国家自然科学基金(22171215,22301225)；湖北省杰出青年基金(2022CFA092)；湖北省自然科学基金(2023AFB034)

Synthesis of 1-Phenylethane-1,2-diol by Photocatalytic C―H Functionalization

Yuanyuan Ping1, Wangqing Kong1,2   

  1. 1 The Institute for Advanced Studies (IAS), Wuhan University, Wuhan 430072, China;
    2 National Demonstration Center for Experimental Chemistry Education (Wuhan University), Wuhan 430072, China
  • Received:2024-08-24 Accepted:2024-10-14 Published:2025-06-20
  • Contact: KONG Wangqing E-mail:wqkong@whu.edu.cn

PDF

293

赞

摘要： 惰性碳氢键的直接官能团化是合成化学领域的前沿挑战之一，被认为是有机合成的“圣杯”。近年来，光氢原子转移(HAT)已发展成为活化惰性碳氢键的重要工具之一。我们以大宗化学品乙二醇与商业化可得的溴苯为原料，通过光氢原子转移/镍协同催化实现了1-芳基-1,2-乙二醇的高效合成。本实验综合性强，操作简便安全，涵盖无水无氧操作、薄层色谱法与快速柱层析操作、气相色谱-质谱联用以及核磁共振检测与解析等多项实验操作。此外，该实验条件温和，原料廉价易得，操作简单且不需要复杂的设备，既能让学生了解有机化学的前沿进展，激发学生学习化学的兴趣和热情，调动学生学习的积极性和主动性，还能使学生的实验技能得到充分锻炼，培养学生的科学素养和探索未知的精神，具有重大的应用价值与教学价值。

关键词: 光氢原子转移, 镍催化, 自由基化学, 1-苯基乙二醇, 有机化学实验

Abstract: Direct functionalization of inert C―H bonds is one of the cutting-edge challenges in synthetic chemistry and is considered the “holy grail” of organic synthesis. In recent years, photohydrogen atom transfer (HAT) has developed into one of the important tools for activating inert C―H bonds. We use bulk chemical ethylene glycol and commercially available bromobenzene as starting materials and achieved an efficient synthesis 1-phenylethane-1,2-diol via photo-HAT/nickel dual catalysis. This comprehensive experiment covers a variety of techniques, including anhydrous and anaerobic procedures, thin-layer chromatography (TLC), flash column chromatography, gas chromatography-mass spectrometry (GC-MS), nuclear magnetic resonance (NMR) analysis, and other experimental operations. The experiment conditions are mild, the raw materials are cheap and readily available, the operation is simple, and no complicated equipment is required. In addition, it can not only enable students to understand the cutting-edge progress of organic chemistry, stimulate students’ interest and enthusiasm in learning chemistry, and improve students’ enthusiasm and initiative, but also enable students to fully exercise their experimental skills, cultivate students’ scientific literacy and spirit of exploring the unknown, and holds significant practical and teaching value.

Key words: Photohydrogen atom transfer, Nickel catalysis, Radical chemistry, 1-Phenylethane-1,2-diol, Organic chemistry experiment