烯烃自由基阴离子的可控产生与转化

doi:10.6023/cjoc202603031

摘要/Abstract

烯烃自由基阴离子作为一类兼具自由基与碳负离子双重反应特性的高活性中间体, 在有机合成领域展现出独特的应用价值. 然而, 由于缺少温和可控的产生方法, 导致其参与的反应类型受限、底物适用范围较窄, 且反应立体选择性难以调控等问题. 因此, 烯烃自由基阴离子的可控生成与高选择性转化面临着多重挑战. 近年来, 随着新型催化体系的持续开发与不断发展, 烯烃自由基阴离子的反应类型已得到初步拓展, 为相关领域的合成研究提供了更多可能性. 本文将从烯烃自由基阴离子的不同生成方式及其参与的多样化转化反应两个维度出发, 简要综述该类中间体的三类主要生成策略——化学还原、电化学还原和光化学还原, 及其在几类重要烯烃转化反应中的研究进展, 并对该领域未来的发展方向进行展望.

关键词: 烯烃官能化, 自由基阴离子, 单电子还原, 自由基反应, 可见光催化

Alkene radical anions are a highly reactive class of intermediates that exhibit the dual reactivity of both radicals and carbanions, and thus hold unique value in organic synthesis. However, the controlled generation and highly selective transformation of these species remain challenging, mainly due to the dearth of efficient methods for their controlled generation, especially in catalytic manner. This resulted in many issues such as difficult stereocontrol, limited substrate scope, and the relatively narrow range of reaction patterns available. In recent years, with the continuous development and advancement of novel catalytic systems, the reaction types of alkene radical anions have been initially expanded, offering more possibilities for synthetic research in related fields. This review briefly summarizes three major strategies for the generation of alkene radical anions—chemical reduction, electrochemical reduction, and photochemical reduction—and discusses their applications in several important alkene transformation reactions from the perspectives of both generation modes and downstream reactivity. Finally, the future development of this field is also discussed.

Key words: alkene functionalization, alkene radical anion, single-electron reduction, radical reaction, visible light photocatalysis

引用此文

张斌, 肖文精, 陈加荣. 烯烃自由基阴离子的可控产生与转化[J]. 有机化学, 2026, 46(4): 1181-1204.

Bin Zhang, Wenjing Xiao, Jiarong Chen. Controlled Generation and Transformations of Alkene Radical Anions[J]. Chinese Journal of Organic Chemistry, 2026, 46(4): 1181-1204.

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图/表 48

图式1. 自由基离子中间体的反应性

Scheme 1. Reactivity of radical ion intermediates

图式2. 烯烃自由基离子中间体的生成与转化

Scheme 2. Overview of the generation and transformations of alkene radical ions

图式3. 碱金属促进的烯烃还原与还原二聚反应

Scheme 3. Alkali-metal-promoted reduction and reductive dimerization of alkenes

图式4. 金属钠介导的烯烃自由基阴离子的二聚羧化反应

Scheme 4. Na-mediated dimeric carboxylation of alkene radical anions

图式5. 碱金属介导的烯烃自由基阴离子的二硅烷化反应

Scheme 5. Alkali metal-mediated disilylation of alkene radical anions

图式6. DTBB催化的芳基烯烃的二锂化反应

Scheme 6. DTBB-catalyzed dilithiation of styrene

图式7. 金属镁促进的烯烃氢酰化反应

Scheme 7. Regioselective Mg-promoted hydroacylation of alkenes

图式8. 金属镁促进的乙烯基三氟甲磺酸酯的还原硅基化反应

Scheme 8. Solvent-controlled reductive coupling of activated vinyl triflates with chlorotrimethylsilane by Mg

图式9. 钠分散体介导的芳基烯烃还原双官能化

Scheme 9. Reductive difunctionalization of aryl alkenes with Na

图式10. 铁(I)配合物介导的富电子烯烃Z→E异构化

Scheme 10. Iron mediated Z→E isomerization of alkenes

图式11. SmI2介导的共轭烯烃的选择性还原反应

Scheme 11. Selective reduction of conjugated olefins mediated by SmI2

图式12. 电催化1,1-二芳基乙烯的氢化还原反应

Scheme 12. Electrochemical reduction of 1,1-diaryl-substituted ethenes

图式13. 氨气作为氢源的电化学加氢反应

Scheme 13. Electrochemical hydrogenation with gaseous ammonia

图式14. 电催化缺电子烯烃的还原氘代反应

Scheme 14. Electrochemical reductive deuteration of electron-deficient alkenes

图式15. 电催化芳基烯烃的还原氘代反应

Scheme 15. Electrochemical reductive deuteration of aryl-substituted alkenes

图式16. 缺电子烯烃的电化学还原酰化反应

Scheme 16. Electrochemical reductive acylation of electron deficient olefins

图式17. 电催化芳基烯烃的酰化反应

Scheme 17. Electrochemical acylation of aryl olefins

图式18. 电催化芳基烯烃, 杂芳烃与未活化脂肪醛的还原偶联及脱芳构化偶联反应

Scheme 18. Electroinduced reductive and dearomative alkene-aldehyde coupling

图式19. 电催化芳基烯烃的羧基氢化反应

Scheme 19. Electrocatalytic hydrocarboxylation of aryl olefin radical anions

图式20. 电催化1,3-二烯与缺电子烯烃的羧基氢化反应

Scheme 20. Electrocatalytic hydrocarboxylation of 1,3-diene and electron deficient olefins

图式21. 二氧化碳参与的烯烃电化学内酰胺化反应

Scheme 21. Electrochemical lactamization with CO2

图式22. 电催化偕二氟烯烃与二氧化碳的脱氟羧化反应

Scheme 22. Electrochemical defluorinative carboxylation of gem-difluoroalkenes with carbon dioxide

图式23. 烯烃的电化学分子内/分子间还原二聚反应

Scheme 23. Electrochemical intra- and intermolecular reductive dimerization of alkenes

图式24. 自由基阴离子分子内环加成反应

Scheme 24. Intramolecular cycloaddition reaction of radical anions

图式25. 自由基阴离子分子内环加成反应机理

Scheme 25. Proposed mechanism for anion radical cycloadditions

图式26. 应用于烯烃单电子还原的强还原光敏剂

Scheme 26. Strongly reducing photosensitizers for the single-electron reduction of alkenes

图式27. 光促进的烯烃自由基阴离子的氢烷氧/氢氰化反应

Scheme 27. Hg lamp-promoted hydroalkoxylation / hydrocyanation of alkene radical anions

图式28. 缺电子烯烃与烯丙基硅烷的光催化烯丙基化反应

Scheme 28. Photocatalytic allylation of electron-deficient alkenes with allylsilanes

图式29. 光酶催化乙烯基吡啶的不对称还原氢化反应

Scheme 29. Photoenzymatic hydrogenation of heteroaromatic olefins

图式30. 双光子光催化芳基烯烃的还原氢化反应

Scheme 30. Reductive activation and hydrofunctionalization of olefins by multiphoton tandem photoredox catalysis

图式31. 双光子光催化芳基烯烃的还原氢化反应机理

Scheme 31. Mechanism of olefin reductive activation via multiphoton tandem photoredox catalysis

图式32. 可见光催化缺电子烯烃的还原氢化反应

Scheme 32. Visible-light-driven reductive hydrogenation of electron-deficient alkenes

图式33. 光催化缺电子烯烃/杂芳烃的还原氢化反应

Scheme 33. Photocatalytic reductive hydrogenation of electron-deficient alkenes/heteroarenes

图式34. 光催化烯烃与醇的亲核加成反应

Scheme 34. Photocatalytic nucleophilic addition of alcohols to alkenes

图式35. 光催化α,β-不饱和酰胺的α-亲核加成反应

Scheme 35. Photocatalytic α-nucleophilic addition to α,β-un- saturated amides

图式36. 光催化烯烃与唑类化合物的马式氢胺化反应

Scheme 36. Photocatalytic Markovnikov hydroamination of alkenes with azoles

图式37. 光催化烯烃/芳烃与CO2的双羧基化反应

Scheme 37. Dicarboxylation of alkenes, allenes and (hetero)arenes with CO2 via visible-light photoredox catalysis

图式38. 光催化烯烃与酮的还原偶联反应

Scheme 38. Photocatalytic reductive coupling of alkenes with ketones

图式39. 光催化烯烃与醛/异氰酸酯/胺/CO2的还原偶联反应

Scheme 39. Photocatalytic reductive coupling of alkenes with aldehydes/isocyanate/amines/CO2

图式40. 光催化烯烃-烯烃还原交叉偶联反应

Scheme 40. Reductive cross-coupling of olefins via a radical anion pathway

图式41. 光催化烯烃的三氟甲基与单氟烯基化反应

Scheme 41. Trifluoromethylation and monofluoroalkenylation of alkenes through radical-radical cross-coupling

图式42. EDA复合物驱动的烯烃与CO₂碳-羧基化反应

Scheme 42. EDA complex-enabled carbo-carboxylation of alkenes with CO₂

图式43. 光催化烯烃自由基阴离子的聚合反应

Scheme 43. Sequential radical-anionic polymerizations via consecutive photo-reduction

图式44. 光催化不饱和酮的[2＋2]环加成反应

Scheme 44. Photocatalytic intra- and intermolecular [2＋2] cycloaddition of enones

图式45. 光铜催化烯烃与亚胺的[2＋2]环加成反应

Scheme 45. Intermolecular [2＋2] imine-olefin photocycloadditions enabled by Cu(I)

图式46. 光/铜协同催化烯烃的羧基胺化与羧基炔化反应

Scheme 46. Metallaphotoredox-catalyzed aminocarboxylation and alkynylcarboxylation of alkenes

图式47. 芳香烯烃自由基阴离子的对映选择性氰基官能化

Scheme 47. Enantioselective cyanofunctionalization of aromatic alkenes via radical anions

图式48. 光/铜协同催化1,3-丁二烯的氢烷氧基化反应

Scheme 48. Stereodivergent hydroalkoxylation of 1,3-dienes via dual photo and copper catalysis

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