| 吴志强,江焕峰,李建晓.化学通报,2026,89(7):874-882,857. |
| “惰性”C(sp2)-Cl键的完美蜕变—以金属催化反应为例 |
| The Perfect Transformation of Inert C(sp2)-Cl Bonds: A Case Study of Metal-Catalyzed Reactions |
| 投稿时间：2026-03-05 修订日期：2026-03-27 |
| DOI： |
| 中文关键词: 芳基氯 金属催化 惰性键 反应活性 催化合成 |
| 英文关键词:aryl chlorides, metal catalysis, inert bonds, reactivity, catalytic synthesis |
| 基金项目:国家重点研发计划项目(2022YFB4101800)、广东省本科高校教学质量与教学改革工程建设项目(464)和广东省基础与应用基础研究基金(2026A1515010288)资助 |
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| 摘要点击次数: 175 |
| 全文下载次数: 49 |
| 中文摘要: |
| 在基础有机化学教材中,芳基氯化物由于C-Cl键的高键能通常被认为是“惰性”化合物,一般条件下难以发生化学反应。本文系统回顾了过渡金属催化芳基氯化物C(sp2)-Cl键从“惰性”到“活性”的蜕变历程。自1998年Fu、Buchwald和Hartwig等人的开创性工作以来,化学家们通过采用富电子、大位阻膦配体或N-杂环卡宾(NHC)配体,有效实现了C(sp2)-Cl键的多样性转化反应。此外,随着镍、铜、铁等廉价金属催化体系不断发展,通过配体工程和预催化剂设计,显著提升了反应的活性和实用性。未来,该领域将趋向于结合人工智能、光催化等新兴技术,开发更高效、绿色、可持续的催化新策略,推动其在合成化学中的广泛应用。因此,将这些前沿进展融入课堂教学,不仅有助于学生理解芳基氯化物的结构特性,而且能够丰富教材现有知识体系,进而拓展学生的专业视野。 |
| 英文摘要: |
| In foundational organic chemistry textbooks, aryl chlorides are often considered "inert -Cl bond, making them generally unreactive under typical conditions. This article systematically reviews the transformative journey of the C(sp2)-Cl bond in aryl chlorides from "inert" to "active" through transition-metal catalysis. Since the pioneering work of Fu, Buchwald, Hartwig, and others in 1998, chemists have successfully achieved diverse transformations of the C(sp2)-Cl bond by employing electron-rich, sterically hindered phosphine ligands or N-heterocyclic carbene (NHC) ligands. Furthermore, with the continuous development of catalytic systems based on inexpensive metals such as nickel, copper, and iron, the activity and practicality have been significantly improved through ligand engineering and pre-catalyst design. In the future, the field is expected to trend toward integrating emerging technologies such as artificial intelligence and photocatalysis to develop more efficient, green, and sustainable catalytic strategies, thereby promoting their broader application in synthetic chemistry. Therefore, incorporating these cutting-edge advances into classroom teaching not only helps students understand the structural characteristics of aryl chlorides but also enriches the existing knowledge framework in textbooks, thereby expanding students" professional perspectives. |
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