杂环化合物脱芳构化[3+2]环加成/环化反应研究进展
1. 信阳师范大学, 新能源科学与技术学院, 河南信阳 464000
2. 河南省核技术应用中心人力资源部, 河南信阳 464000
3. 信阳师范大学, 化学化工学院, 河南信阳 464000
| 摘 要： | 杂环化合物的脱芳构化反应是构建复杂化合物骨架的重要手段，在药物化学及功能材料领域具有重要的应用价值。其中脱芳构化[3+2]环加成反应策略，因其原子经济性高和合成步骤简洁性的特点，已经成为高效构筑多取代杂环化合物骨架的研究热点。本文系统综述了近年来该领域的重要进展，重点探讨过渡金属催化、有机小分子催化等新型催化体系在吲哚、吡咯、呋喃及喹啉等代表性杂环底物中的适用性，重点分析了催化剂结构、配体效应、溶剂及添加剂对反应选择性（包括化学选择性、区域选择性、立体选择性）的影响规律，并总结了近期在不对称脱芳构化[3+2]环加成方面取得的突破性成果。展望未来，开发新型活化模式、借助理论计算精准调控电子效应、设计多组分串联反应，以及结合人工智能加速催化剂筛选与条件优化，将成为突破方向，有望推动该策略在天然产物全合成及高附加值功能分子创制中的实际应用。 |
| 关 键 词： | 脱芳构化反应; [3+2]环加成; 过渡金属催化; 不对称催化 |
| DOI： | 10.57237/j.cse.2026.02.002 |
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收稿日期: 2026-06-05
接受日期: 2026-07-01
在线出版日期: 2026-07-28
Research Advances in Dearomatization [3+2] Cycloaddi-tion/Cyclization Reactions of Heterocyclic Compounds
1. School of New Energy Science and Technology, Xinyang Normal University, Xinyang 464000, China
2. Human Resources Department of Henan Nuclear Technology Application Center, Xinyang 464000, China
3. College of Chemistry and Chemical Engineering, Xinyang Normal University, Xinyang 464000, China
| Abstract: | The dearomatization reaction of heterocyclic compounds serves as a pivotal strategy for constructing complex cyclic frameworks, demonstrating significant application potential in pharmaceutical chemistry and functional materials science. Particularly, the dearomatization-enabled [3+2] cycloaddition strategy has emerged as a research hotspot for efficiently building multi-substituted heterocyclic architectures, owing to its inherent advantages of high atom economy and synthetic step-efficiency. This review systematically summarizes recent important advances in this field, with a particular focus on the applicability of novel catalytic systems—including transition-metal catalysis and organocatalysis—to representative heterocyclic substrates such as indoles, pyrroles, furans, and quinolines. It places special emphasis on analyzing the effects of catalyst structure, ligand effects, solvents, and additives on reaction selectivity, encompassing chemoselectivity, regioselectivity, and stereoselectivity, and also summarizes the breakthrough achievements recently made in asymmetric dearomative [3+2] cycloadditions. Looking forward, the development of novel activation modes, precise regulation of electronic effects aided by theoretical calculations, design of multicomponent cascade reactions, and the integration of artificial intelligence to accelerate catalyst screening and condition optimization will represent key directions for future breakthroughs. These efforts are expected to promote the practical application of this strategy in the total synthesis of natural products and the creation of high‑value‑added functional molecules. |
| Keywords: | Dearomatization Reactions; [3+2] Cycloaddition; Transition-metal Catalysis; Asymmetric Catalysis |
基金
| 1. | 河南省科技计划项目(No. 242102310298) |
| 2. | 河南省科技攻关项目(No. 252102320334) |
| 3. | 河南省高等学校重点科研项目(No. 25A150020) |
| 4. | 信阳师范大学青年科研基金项目资助(No.2025-QN-002)资助项目 |
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