光催化自由基介导的内酯合成研究进展

doi:10.6023/cjoc202512036

摘要/Abstract

内酯是一类重要的化合物, 广泛存在于许多天然产物和药物分子中. 因为其独特的性质和广泛的应用, 有机化学家们对它的合成做了许多研究. 近年来, 光催化和自由基化学的快速发展为内酯的合成提供了许多新思路. 此综述将从分子内环化和分子间环加成反应两个方面, 对光介导的自由基历程合成内酯的工作进行梳理, 总结并归纳它们的机理和优势, 希望能为该领域提供新的研究视角.

关键词: 内酯, 光催化, 自由基, 单电子转移

Lactones represent a significant class of compounds that are widely present in various natural products and pharmaceutical molecules. Due to their distinctive properties and broad applications, organic chemists have conducted extensive research on their synthesis. In recent years, the rapid development of photocatalysis and radical chemistry has provided many new strategies for the synthesis of lactones. This review is organized into two main approaches: intramolecular cyclization and intermolecular cycloaddition reactions. This review aims to discuss the mechanisms and advantages of these methodologies, offering new perspectives for further research in this field.

Key words: lactones, photocatalysis, radicals, single electron transfer

引用此文

余宁, 周于强, 魏晔. 光催化自由基介导的内酯合成研究进展[J]. 有机化学, 2026, 46(4): 1222-1254.

Ning Yu, Yuqiang Zhou, Ye Wei. Recent Advances in Photocatalytic Radical-Mediated Lactone Synthesis[J]. Chinese Journal of Organic Chemistry, 2026, 46(4): 1222-1254.

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图/表 47

图式1. 内酯在药物与生物活性分子中的典型例子

Scheme 1. Typicaexamples of lactones in pharmaceuticals and bioactive molecules

图式2. 通过可见光光催化芳基内酯化合成二取代丁内酯

Scheme 2. Synthesis of disubstituted butyrolactones through a visible light photocatalytic arylation lactonization

图式3. 通过光还原烷基内酯化合成烷基取代的内酯

Scheme 3. Synthesis of alkyl substituted lactone through photoredox catalyzed alkylation lactonization

图式4. 通过光催化二氧化硫的插入合成磺酰基取代的内酯

Scheme 4. Generation of sulfonated lactones through photocatalystic insertion of sulfur dioxide

图式5. 通过二氟烷基酯化反应合成内酯

Scheme 5. Synthesis of lactones through difluoroalkylesterification

图式6. 通过有机光催化碳杂官能化合成内酯

Scheme 6. Synthesis of lactones through organophotocatalytic carboheterofunctionalization

图式7. 通过氢原子转移自由基偶联合成内酯

Scheme 7. Synthesis of lactones through atom transfer radical coupling

图式8. 通过光还原和铜的协同催化合成内酯

Scheme 8. Synthesis of lactones through cooperative photoredox and copper catalysis

图式9. 通过烯酸的有氧脱氢内酯化合成内酯

Scheme 9. Synthesis of lactones through the aerobic dehydrogenative lactonization of alkenoic acids

图式10. 通过烯酮的环化反应合成内酯

Scheme 10. Synthesis of lactones through ketyl-olefin cyclizations

图式11. 通过芳酰腙的光催化自由基级联反应合成内酯

Scheme 11. Synthesis of lactones through photocatalytic radical cascade reaction of aroylhydrozones

图式12. 通过烷氧羰基自由基环化反应合成内酯

Scheme 12. Synthesis of lactones through an alkoxycarbonyl radical cyclization protocol

图式13. 通过环化炔基化反应合成内酯

Scheme 13. Synthesis of lactones through a cyclizative alkynylation

图式14. 通过丙二烯烷氧羰基化合成内酯

Scheme 14. Synthesis of lactones through allene alkoxycarbonylations

图式15. 通过铁光氧化还原双催化合成内酯

Scheme 15. Synthesis of lactones through Iron/photoredox dual catalysis

图式16. 通过自由基螺并环化反应合成内酯

Scheme 16. Synthesis of lactones through radical spirocyclization cascades

图式17. 通过C—H内酯化合成内酯

Scheme 17. Synthesis of lactones through C—H lactonization of carboxylic acid

图式18. 通过对映选择性光醇化/Diels-Alder反应合成内酯

Scheme 18. Synthesis of lactones through Enantioselective photoenolization/Diels-Alder reaction

图式19. 通过2-酰基苯甲醛环异构化/加成级联反应合成内酯

Scheme 19. Synthesis of lactones through cycloisomerization/addition cascades of 2-acyl benzaldehydes

图式20. 通过亚烷基环丙烷的级联环化反应合成内酯

Scheme 20. Synthesis of lactones through cascade cyclization reactions of alkylidenecyclopropanes

图式21. 通过光环化合成氧杂大环内酯

Scheme21. Synthesis of macrocyclic oxalactones through photocyclization

图式22. 通过自由基光环化合成大环内酯

Scheme 22. Synthesis of macrocyclic lactones through radical photocyclization

图式23. 通过环酮的氧化扩环合成大环内酯

Scheme 23. Synthesis of macrocyclic lactones through oxidative ring expansion of cyclic ketones

图式24. 通过扩环/氨基羰基化级联反应合成大环内酯

Scheme 24. Synthesis of macrocyclic lactones through ring expansion/aminocarbonylation cascade

图式25. 通过可见光介导的大环化反应合成内酯

Scheme 25. Synthesis of lactones through visible light mediated macrocyclization

图式26. 通过羟基醛的C—H溴化合成大环内酯

Scheme 26. Synthesis of macrocyclic lactones through hydroxyaldehydes of C—H bromination

图式27. 通过光氧化还原催化烯烃的双官能团化合成内酯

Scheme 27. Synthesis of lactones through alkene difunctionalization with photoredox catalysis

图式28. 通过光还原催化烯烃羟基二氟乙酰化反应合成二氟内酯

Scheme 28. Synthesis of difluorolactones through photoredox catalyzed hydroxydifluoroacetylation

图式29. 通过烯烃和烯烃的偶联合成δ-内酯

Scheme 29. Synthesis of δ-lactones through alkene-alkene coupling

图式30. 通过自由基极性交叉环加成反应合成内酯

Scheme 30. Synthesis lactones through polar radical crossover cycloaddition reactions

图式31. 通过自由基极性交叉环加成反应合成α-苄氧基氨基γ-丁内酯

Scheme 31. Synthesis of α-benzyloxyamino-γ-butyrolactones through polar radical crossover cycloaddition reactions

图式32. 通过α,β-不饱和羧酸和烯烃的[3＋2]环加成反应合成内酯

Scheme 32. Synthesis of lactones through the [3＋2] cycloaddition of α,β-unsaturated carboxylic acids with olefins

图式33. 通过碘乙酸和烯烃的加成反应合成内酯

Scheme 33. Synthesis lactones through the addition of iodoacetic acid in olefins

图式34. 通过烯烃的二氟烷基化内酯化合成内酯

Scheme 34. Synthesis of lactones through difluoroalkylation lactonization of alkenes

图式35. 通过碘试剂和烯烃的原子转移自由基加成反应合成内酯

Scheme 35. Synthesisof lactones through the atom transfer radical additions of iodo reagents and alkenes

图式36. 通过CDFA和α-卤代羧酸的光氧化活化合成内酯

Scheme 36. Synthesis of lactones through photoredox activation of CDFA and α-halo carboxylic acids

图式37. 通过醇的碳烷基化反应合成内酯

Scheme 37. Synthesis of lactones through C-alkylation of alcohols

图式38. 通过醇的光有机催化合成内酯

Scheme 38. Synthesis of lactones through photoorganocatalytic of alcohols

图式39. 通过α-羰基烷基卤化物和烯烃合成内酯

Scheme 39. Synthesis of lactones through alkenes with α-carbonyl alkyl halides

图式40. 通过酸酐的光还原活化合成内酯

Scheme 40. Synthesis of lactones through photoredox activation of anhydrides

图式41. 通过肉桂醇的三官能化合成内酯

Scheme 41. Synthesis of lactones through trifunctionalization of cinnamyl alcohols

图式42. 通过双环[1.1.0]丁烷的环化反应合成内酯

Scheme 42. Synthesis of lactones through cyclization of bicyclo[1.1.0] butanes

图式43. 通过吩噻嗪亚砜作为活性光催化剂合成内酯

Scheme 43. Synthesis of lactones through phenothiazine sulfoxides as active photocatalysts

图式44. 通过光化学双自由基偶联合成内酯

Scheme 44. Synthesis of lactones through photochemical dual radical coupling

图式45. 通过酰胺的C-H官能化合成内酯

Scheme 45. Synthesis of lactones through C-H functionalization of amides

图式46. 通过烯烃的羧基环化合成内酯

Scheme 46. Synthesis of lactones through carboxy cyclization of alkene

反应类型	光敏剂类型	底物类型	产率
分子内环化合成五元环或六元环内酯	钌, 铱, 铜, 铁, 钪, 小分子光敏剂	烯酸及其衍生物, 草酸衍生物, 醛, 酮, 羟胺衍生物, 羧酸及其衍生物	良好至优异
分子内环化合成中环内酯	铱	亚甲基环丙烷的溴代物	良好
分子内环化合成大环内酯	铈, 铜, 小分子光敏剂	不饱和酯, 环酮, 半缩醛过氧化物	部分产率低
分子间环加成反应合成五元环或六元环内酯	钌, 铱, 小分子光敏剂, 酮酸	烯烃, 不饱和羧酸及其衍生物, 卤代羧酸及其衍生物, 二羰基化合物	良好至优异
分子间环加成反应合成中环内酯	铱, 小分子光敏剂	羟胺衍生物, 烯烃	良好

表1. 代表性方法对比表

Table 1. Representative methods comparison table

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