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 |
| DOI: | 10.57237/j.cse.2026.02.002 |
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Received: 5 June 2026
Accepted: 1 July 2026
Published Online: 28 July 2026
Funding
| 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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