共轭二烯参与的[4＋1]环加成反应研究进展

doi:10.6023/cjoc202407043

摘要/Abstract

五元环是广泛存在于天然产物、药物和功能材料中的一类重要结构单元, 也是有机合成中常用的重要中间体和药物开发的优选骨架. 因此, 五元环化合物的高效合成一直是有机合成领域的重要研究方向之一. 廉价易得、结构多样的共轭二烯参与的[4＋1]环加成反应是一种具有步骤经济性的直接构建五元碳环和杂环化合物的高效方法和策略, 备受有机合成界的青睐. 近年来, 随着过渡金属催化体系和“一原子”合成子前体的开发, 此类将简单易得原料转化成结构复杂和官能团多样化的五元环状分子的[4＋1]环加成反应得到了较快的发展, 很多优秀的成果被报道出来. 详细介绍了共轭二烯与“一原子”合成子(一氧化碳、卡宾、硅宾以及氮宾)的[4＋1]环加成反应的研究进展, 并按照合成子的类型进行了分类讨论, 最后总结了该领域存在的挑战, 展望了未来的研究方向.

关键词: [4＋1]环加成反应, 共轭二烯, 卡宾, 硅宾, 锗宾, 氮宾, 五元环化合物

Five-membered ring motifs widely exist in many natural products, pharmaceuticals and organic materials, and are also important intermediates in organic synthesis and core structures for drug development. Therefore, highly efficient approaches for the synthesis of five-membered cyclic compounds are in high demand. [4＋1] cycloaddition of readily available conjugated diene provides an efficient and straightforward strategy to construct five-membered carbo- and heterocyclic compounds in an atom-economic manner, and have therefore attracted more attention from the synthetic community. In recent years, duo the significant advances in transition-metal catalysis and precursors of one-atom synthons, [4＋1] cycloadditions, which convert simple and readily accessible substrates into complex and diverse five-membered ring molecules, are rapidly growing and a series of excellent achievements have been reported. This review presents the progress in [4＋1] cycloaddition reactions of conjugated diene with various one-atom synthons involving carbon monoxide (CO), carbenes, silylenes, germylenes and nitrenes. The reactions and their mechanisms are discussed according to the types of one-atom synthons. Furthermore, the challenges and future development trends in this field are also prospected.

Key words: [4＋1] cycloaddition, conjugated diene, carbene, silylene, germylene, nitrene, five-membered cyclic compound

引用此文

张业飞, 唐勇, 周友运. 共轭二烯参与的[4＋1]环加成反应研究进展[J]. 有机化学, 2025, 45(1): 1-21.

Yefei Zhang, Yong Tang, You-Yun Zhou. Progress in [4＋1] Cycloadditions of Conjugated Dienes[J]. Chinese Journal of Organic Chemistry, 2025, 45(1): 1-21.

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图/表 31

图1. 含有五元碳环和杂环结构的天然产物、药物和功能材料

Figure 1. Natural product, pharmaceuticals and functional materials containing five-membered carbo- and heterocyclic structures

图2. 五元碳环和杂环化合物合成的常见策略

Figure 2. General strategies for the synthesis of five-membered carbo- and heterocyclic compounds

图式1. 三羰基铁-共轭二烯配合物的分子内[4＋1]环加成反应

Scheme 1. Intramolecular [4＋1] cycloaddition of dienetricarbonyl iron-butadiene complexes

图式2. 铑催化环丙烷封端的1,3-共轭二烯与CO的[4＋1]环加成反应

Scheme 2. Rh-catalyzed [4＋1] cycloadditions of cyclopropyl- caped 1,3-dienes with CO

图式3. 共轭二烯与卡宾的[4＋1]环加成反应

Scheme 3. [4＋1] cycloadditions of 1,3-dienes with carbenes

图式4. 铑催化2-硅氧基-1,3-共轭二烯与重氮的[4＋1]环加成反应

Scheme 4. Rh-catalyzed [4＋1] cycloaddition of 2-siloxy-1,3-dienes with diazo compounds

图式5. 二烷氧基卡宾的产生

Scheme 5. Generation of dimethoxycarbenes

图式6. 贫电子共轭二烯与二烷氧基卡宾的[4＋1]环加成反应

Scheme 6. [4＋1] cycloaddition of electron-deficient dienes with dialkoxycarbenes

图式7. 二烷氧基卡宾的分子内[4＋1]环加成反应机理途径

Scheme 7. Mechanistic pathways of intramolecular [4＋1] cycloaddition of dialkoxycarbenes

图式8. 分子内[4＋1]环加成反应在胡萝卜醇合成中的应用

Scheme 8. Intramolecular [4＋1] cycloaddition: application to the synthesis of carotol

图式9. 手性铑催化重氮与共轭二烯的对映选择性的、形式上的[4＋1]环加成反应

Scheme 9. Chiral Rh-catalyzed enantioselective formal [4＋1] cycloaddition of diazooxindoles with 1,3-dienes

图式10. 芳基重氮乙酸酯与共轭二烯的对映选择性的、形式上的[4＋1]环加成反应

Scheme 10. Enantioselective formal [4＋1] cycloaddition of diazoarylacetates with 1,3-dienes

图式11. 1,1-二溴-2,2-二苯基环丙烷与共轭二烯的[4＋1]环加成反应

Scheme 11. [4＋1] cycloaddition of 1,1-dibromo-2,2-diphenyl- cyclopropane with 1,3-dienes

图式12. Cu(I)催化溴代氟乙酸钠与1,3-二烯的形式上的[4＋1]环加成反应

Scheme 12. Cu(I)-catalyzed formal [4＋1] cycloaddition of 1,3-dienes with sodium bromodifluoroacetate

图式13. 双核镍催化还原1,1-二氯烯烃与共轭二烯的[4＋1]环加成反应

Scheme 13. Dinickel-catalyzed reductive [4＋1] cycloaddition of 1,1-dichloroalkenes with 1,3-dienes

图式14. C2手性双核镍催化1,1-二氯烯烃和共轭二烯的对映选择性[4＋1]环加成反应

Scheme 14. C2?symmetric dinickel-catalyzed enantioselective [4＋1] cycloaddition of 1,1-dichloroalkene with 1,3-dienes

图式15. Fischer型卡宾配合物与山梨酸甲酯的形式上的[4＋1]环加成反应

Scheme 15. Formal [4＋1] cycloaddition of Fischer carbene complexes with methyl sorbate

图式16. Fischer型卡宾配合物与1,3-二氨基-1,3-丁二烯的形式上的[4＋1]环加成反应

Scheme 16. Formal [4＋1] cycloaddition of Fischer carbene complexes with 1,3-diamino-1,3-dienes

图式17. Fischer型卡宾配合物与电中性共轭二烯的形式上的[4＋1]环加成反应

Scheme 17. Formal [4＋1] cycloaddition of Fischer carbene complexes with electronically neutral 1,3-dienes

图式18. Fischer型卡宾配合物与1-氨基-1,3-二烯的形式上的[4＋1]环加成反应

Scheme 18. Formal [4＋1] cycloaddition of Fischer carbene complexes with 1-amino-1,3-dienes

图式19. 铬氨基卡宾配合物分子内形式上的[4＋1]环加成反应

Scheme 19. Formal intramolecular [4＋1] cycloaddition of chromium aminocarbenes

图式20. 丁二烯与四氯硅烷的形式上的双[4＋1]环加成反应

Scheme 20. Double [4＋1] cycloaddition of 1,3-butadiene with silicon tetrachloride

图式21. 丁二烯与二氯硅烷的[4＋1]环加成反应反应机理

Scheme 21. Mechanism of [4＋1] cycloaddition of 1,3-butadi- ene with dichlorosilanes

图式22. 1,1-二锂-2,3,4,5-四苯基环戊二烯硅烷与共轭二烯的形式上的[4＋1]环加成反应

Scheme 22. Formal [4＋1] cycloaddition of 1,1-dilithio-2,3,4,5-tetraphenylsilole with 1,3-dienes

图式23. 钯催化(氨基硅基)硼酸酯与共轭二烯[4＋1]环加成反应

Scheme 23. Pd-catalyzed [4＋1] cycloaddition of (aminosilyl)- boronic esters with 1,3-dienes

图式24. 钯催化(氨基硅基)硼酸酯与2-乙烯基吲哚的[4＋1]环加成反应

Scheme 24. Pd-catalyzed [4＋1] cycloaddition of (aminosilyl)boronic esters with 2-vinylindoles

图式25. 无过渡金属参与的二苯基硅宾转移反应合成硅杂环戊烯

Scheme 25. Synthesis of silacyclopent-3-enes by transition-metal-free diphenylsilylene transfer

图式26. 镍催化还原二氯硅烷与共轭二烯的[4＋1]环加成反应

Scheme 26. Ni-catalyzed reductive [4＋1] cycloaddition of dichlorosilanes with 1,3-dienes

图式27. 二甲基二氯锗烷与共轭二烯的[4＋1]环加成反应

Scheme 27. [4＋1] cycloaddition of dichlorodimethylgermane with 1,3-dienes

图式28. 1,2-双(二茂铁基)二锗烷与2,3-二甲基-1,3-丁二烯的[4＋1]环加成反应

Scheme 28. [4＋1] Cycloaddition of 1,2-bis(ferrocenyl)digermene with 2,3-dimethyl-1,3-butadiene

图式29. 铜催化氮宾前体与共轭二烯的形式上的[4＋1]环加成反应

Scheme 29. Cu-catalyzed formal [4＋1] cycloaddition of nitrene precursors with 1,3-dienes

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