Recent Advances in Hypervalent Iodine Mediated Radical Fluoroalkylative Difunctionalization of Alkenes

doi:10.6023/cjoc202601040

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (4): 1390-1427.DOI: 10.6023/cjoc202601040 Previous Articles Next Articles

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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

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)

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

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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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Fig. & Tab. 43

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

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

Scheme 3. NHC catalyzes trifluoromethylation reaction of aryl alkenes 3

Scheme 4. Trifluoromethylcyclization reaction of alkenes 6

Scheme 5. Trifluoromethylalkylation reaction of alkenes 8

Scheme 6. Trifluoromethylcyanation reaction of alkenes 11

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

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

Scheme 9. Copper catalyzed asymmetric trifluoromethylcyanation reaction of alkenes 23

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

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

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

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

Scheme 14. Copper-catalysed asymmetric trifluoromethylalkynylation of alkenes 39

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

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

Scheme 17. Trifluoromethylamination reaction of alkenes 47

Scheme 18. Remote migration reaction of heteroaryl alkenes 49

Scheme 19. Trifluoromethylarylation reaction of alkenes 51

Scheme 20. Trifluoromethylenylation reaction of alkenes 53

Scheme 21. Trifluoromethylenylation reaction of alkenes 55

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

Scheme 23. Trifluoromethylvulcanization reaction of alkenes 59

Scheme 24. Trifluoromethylamination of alkenes 65

Scheme 25. Trifluoromethylazolation of alkenes 68

Scheme 26. Trifluoromethylvulcanization reaction of alkenes 71

Scheme 27. Trifluoromethylcyanation reaction of alkenes 73

Scheme 28. Photocatalytic oxytrifluoromethylation reaction of alkenes 75

Scheme 29. Trifluoromethylnitrogenheterocyclization reaction of alkene 77

Scheme 30. Trifluoromethylinternalesterification reaction of alkenes 80

Scheme 31. Trifluoromethylacylation reaction of alkenes 82

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

Scheme 33. Trifluoromethylinternalesterification reaction of alkenes 90

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

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

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

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

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

Scheme 39. ZnI2-catalyzed aminotrifluoromethylation cyclization of alkenes 103

Scheme 40. Trifluoromethylthiocyanation of alkenes 106

Scheme 41. Difluoromethylarylation reaction of alkenes 109

Scheme 42. Difluoromethylarylation reaction of alkenes 112

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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