高价碘试剂介导的烯烃自由基氟烷基双官能化研究进展

doi:10.6023/cjoc202601040

有机化学 ›› 2026, Vol. 46 ›› Issue (4): 1390-1427.DOI: 10.6023/cjoc202601040 上一篇下一篇

综述与进展

高价碘试剂介导的烯烃自由基氟烷基双官能化研究进展

吴少华^a^,^†, 龚帆^a^,^†, 曹柱^a^,^b^,^*(), 邓清海^a^,^b^,^*()

^a 上海师范大学化学与材料科学学院上海 200234
^b 中国科学院上海有机化学研究所先进氟氮材料全国重点实验室先进氟氮材料全国重点实验室上海 200032

收稿日期:2026-01-24 修回日期:2026-02-25 发布日期:2026-03-13
通讯作者: 曹柱, 邓清海
作者简介:
^†共同第一作者
基金资助:
国家自然科学基金(22371187); 国家自然科学基金(22501184); 上海市自然科学基金(22ZR1445200); 上海市自然科学基金(25ZR1402406); 上海稀土功能材料重点实验室和上海仿生催化前沿科学中心资助项目; “111”光化学与能源材料创新人才引进基地(D18020); 上海绿色能源化工工程技术研究中心(18DZ2254200)

Recent Advances in Hypervalent Iodine Mediated Radical Fluoroalkylative Difunctionalization of Alkenes

Shaohua Wu^a, Fan Gong^a, Zhu Cao^a^,^b^,^*(), Qinghai Deng^a^,^b^,^*()

^a College of Chemistry and Materials Science, Shanghai Normal University, Shanghai 200234
^b State Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032

Received:2026-01-24 Revised:2026-02-25 Published:2026-03-13
Contact: Zhu Cao, Qinghai Deng
About author:
^†These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(22371187); National Natural Science Foundation of China(22501184); Natural Science Foundation of Shanghai(22ZR1445200); Natural Science Foundation of Shanghai(25ZR1402406); Shanghai Key Laboratory of Rare Earth Functional Materials, and the Shanghai Frontiers Science Center of Biomimetic Catalysis.; Chinese Education Ministry Key Laboratory and International Joint Laboratory on Resource Chemistry, the “111” Innovation and Talent Recruitment Base on Photochemical and Energy Materials(D18020); Shanghai Engineering Research Center of Green Energy Chemical Engineering(18DZ2254200)

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摘要/Abstract

近几十年来, 高价碘试剂作为一类环境友好、反应活性可调的合成子, 在烯烃自由基氟烷基双官能化反应中展现出显著优势. 此文系统综述了近年来基于环状高价碘试剂(Togni-I、Togni-II)及非环状高价碘试剂参与的烯烃氟烷基双官能化研究进展. 该类反应通过自由基加成、交叉偶联和迁移环化等途径, 将三氟甲基、二氟甲基等氟烷基化与(杂)芳基化、氰基化、胺化和叠氮化等其他官能团化过程相结合, 实现了对烯烃的一步双官能化, 成功构建了一系列含氟杂环及具有手性中心的复杂氟化分子骨架. 围绕环状与非环状高价碘试剂, 重点阐述了各类催化体系在调控反应选择性与普适性中的策略及机理, 为今后高价碘氟烷基化试剂在有机合成中的应用提供参考.

关键词: 高价碘试剂, 烯烃, 氟烷基化, 双官能化

In recent decades, hypervalent iodine reagents have emerged as a class of environmentally benign and tunable reactivity synthons, demonstrating remarkable advantages in radical fluoroalkylative difunctionalization of alkenes. This review systematically summarizes the recent advances in alkene difunctionalization involving cyclic hypervalent iodine reagents (Togni-I, Togni-II) and acyclic hypervalent iodine reagents. Through pathways such as radical addition, cross-coupling, migratory cyclization, and others, these reactions integrate fluoroalkylation, including trifluoromethylation, difluoromethylation, etc., with other functionalization processes such as (hetero)arylation, cyanation, amination, and azidation, achieving one-step difunctionalization of alkenes. This strategy has successfully constructed a series of fluorine-containing heterocycles and complex fluorinated molecular frameworks with chiral centers. Organized around cyclic and acyclic hypervalent iodine reagents, this article focuses on the strategies and mechanisms of various catalytic systems in controlling reaction selectivity and generality, aiming to provide insights for future applications of hypervalent iodine fluoroalkylation reagents in organic synthesis.

Key words: hypervalent iodine reagents, alkenes, fluoroalkylation, difunctionalization

引用此文

吴少华, 龚帆, 曹柱, 邓清海. 高价碘试剂介导的烯烃自由基氟烷基双官能化研究进展[J]. 有机化学, 2026, 46(4): 1390-1427.

Shaohua Wu, Fan Gong, Zhu Cao, Qinghai Deng. Recent Advances in Hypervalent Iodine Mediated Radical Fluoroalkylative Difunctionalization of Alkenes[J]. Chinese Journal of Organic Chemistry, 2026, 46(4): 1390-1427.

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图/表 43

图式1. 高价碘试剂参与的烯烃自由基氟烷基双官能化

Scheme 1. Olefin radical fluoroalkyl bifunctionalization invol- ved by the hypervalent iodine reagent

图式2. 铜催化1,3-烯炔-ACP的三组分加成-环异构化双官能化反应

Scheme 2. Copper-catalyzed three-component addition-cycloisomerization difunctionalization reaction of 1,3 enyne-ACPs

图式3. NHC催化芳基烯烃3的三氟甲基化反应

Scheme 3. NHC catalyzes trifluoromethylation reaction of aryl alkenes 3

图式4. 烯烃6的三氟甲基环化反应

Scheme 4. Trifluoromethylcyclization reaction of alkenes 6

图式5. 烯烃8的三氟甲基烷基化反应

Scheme 5. Trifluoromethylalkylation reaction of alkenes 8

图式6. 烯烃11的三氟甲基氰基化反应

Scheme 6. Trifluoromethylcyanation reaction of alkenes 11

图式7. 铜(I)与手性磷酸协同催化烯烃14的三氟甲基化反应

Scheme 7. Trifluoromethylation reaction of alkenes 14 catalyzed by copper (I) and chiral phosphoric acid

图式8. 铜催化烯烃19的不对称三氟甲基氰基化和三氟甲基醚化反应

Scheme 8. Copper catalyzed asymmetric trifluoromethylcyanation and trifluoromethyletherification reaction of alkenes 19

图式9. 铜催化烯烃23的不对称三氟甲基氰基化反应

Scheme 9. Copper catalyzed asymmetric trifluoromethylcyanation reaction of alkenes 23

图式10. 铜与手性磷酸协同催化烯烃25与肼的不对称三氟甲基胺化反应

Scheme 10. Asymmetric trifluoromethylamination reaction of alkene 25 with hydrazine catalyzed by copper and chiral phosphoric acid

图式11. 手性钒配合物催化的不对称自由基型三氟甲基醚化反应

Scheme 11. Asymmetric radical-type trifluoromethyletherification reaction catalysed by chiral vanadium complexes

图式12. 手性磷酸催化的可见光诱导烯胺31的不对称三氟甲基胺化及三氟甲基醚化反应

Scheme 12. CPA-catalysed visible-light-induced asymmetric trifluoromethylamination and trifluoromethyletherification reaction of enamines 31

图式13. 铜催化烯烃37的不对称自由基三氟甲基氯化反应

Scheme 13. Copper catalyzed asymmetric radical trifluoromethylchlorination reaction of alkenes 37

图式14. 铜催化烯烃39不对称三氟甲基炔基化反应

Scheme 14. Copper-catalysed asymmetric trifluoromethylalkynylation of alkenes 39

图式15. NHC催化烯醛42的三氟甲基δ-内酯化反应

Scheme 15. Trifluoromethyl-δ-lactonization reaction of alkenal 42 catalyzed by NHC

图式16. NHC催化烯烃3不对称三氟甲基酰基化反应

Scheme 16. NHC-catalysed asymmetric trifluoromethylacylation reaction of alkenes 3

图式17. 烯烃47的三氟甲基胺化反应

Scheme 17. Trifluoromethylamination reaction of alkenes 47

图式18. 三氟甲基自由基参与的杂芳基烯烃49的远程迁移反应

Scheme 18. Remote migration reaction of heteroaryl alkenes 49

图式19. 烯烃51的三氟甲基芳基化反应

Scheme 19. Trifluoromethylarylation reaction of alkenes 51

图式20. 烯烃53的三氟甲基烯基化反应

Scheme 20. Trifluoromethylenylation reaction of alkenes 53

图式21. 烯烃55的三氟甲基烯基化反应

Scheme 21. Trifluoromethylenylation reaction of alkenes 55

图式22. 1,6-二烯57三氟甲基化/环化/远程氧化反应

Scheme 22. Tandem trifluoro methylation/cyclization/remote oxidation of 1,6-dienes 57

图式23. 烯烃59的三氟甲基硫化反应

Scheme 23. Trifluoromethylvulcanization reaction of alkenes 59

图式24. 烯烃65的三氟甲基胺化反应

Scheme 24. Trifluoromethylamination of alkenes 65

图式25. 烯烃68的三氟甲基唑化反应

Scheme 25. Trifluoromethylazolation of alkenes 68

图式26. 烯烃71的三氟甲基硫化反应

Scheme 26. Trifluoromethylvulcanization reaction of alkenes 71

图式27. 烯烃73的三氟甲基氰基化反应

Scheme 27. Trifluoromethylcyanation reaction of alkenes 73

图式28. 光催化烯烃75的氧三氟甲基化反应

Scheme 28. Photocatalytic oxytrifluoromethylation reaction of alkenes 75

图式29. 烯烃77的三氟甲基氮杂环化反应

Scheme 29. Trifluoromethylnitrogenheterocyclization reaction of alkene 77

图式30. 烯烃80的三氟甲基内酯化反应

Scheme 30. Trifluoromethylinternalesterification reaction of alkenes 80

图式31. 烯烃82的三氟甲基酰化反应

Scheme 31. Trifluoromethylacylation reaction of alkenes 82

图式32. 烯烃84、86和88的三氟甲基化/(双)环化反应

Scheme 32. Trifluoromethylation/(bi)cyclization of alkenes 84, 86 and 88

图式33. 烯烃90的三氟甲基内酯化反应

Scheme 33. Trifluoromethylinternalesterification reaction of alkenes 90

图式34. 三氟甲基自由基参与的烯烃92的不对称自由基级联反应

Scheme 34. Asymmetric radical cascade reaction of alkenes 92 involving trifluoromethyl radical

图式35. 非血红素铁酶催化的不对称自由基三氟甲基叠氮化反应

Scheme 35. Asymmetric radical trifluoromethylazidation reaction catalyzed by non-heme iron enzyme

图式36. 铜催化的烯丙胺CO2的不对称交叉偶联三氟甲基化反应

Scheme 36. Copper-catalyzed asymmetric cross-coupling trifluoromethylation reaction of allylamines with CO2

图式37. 铜取代非血红素酶的定向进化用于烯烃98的不对称三氟甲基环化

Scheme 37. Directed evolution of copper-replacing non-heme enzymes for asymmetric trifluoromethylcyclization reaction of alkenes 98

图式38. 铜催化1,3-二烯100的三氟甲基胺化反应

Scheme 38. Copper catalyzed trifluoromethylamination reaction of 1,3-dienes 100

图式39. ZnI2催化烯烃103的氨基三氟甲基环化反应

Scheme 39. ZnI2-catalyzed aminotrifluoromethylation cyclization of alkenes 103

图式40. 烯烃106的三氟甲基硫氰基化反应

Scheme 40. Trifluoromethylthiocyanation of alkenes 106

图式41. 烯烃109的二氟甲基芳基化反应

Scheme 41. Difluoromethylarylation reaction of alkenes 109

图式42. 烯烃112的二氟甲基芳基化反应

Scheme 42. Difluoromethylarylation reaction of alkenes 112

图式43. 光催化烯烃114的二氟烷基化反应

Scheme 43. Photocatalytic difluoroalkylation reaction of alkene 114

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高价碘试剂介导的烯烃自由基氟烷基双官能化研究进展

Recent Advances in Hypervalent Iodine Mediated Radical Fluoroalkylative Difunctionalization of Alkenes

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