脱氟反应的研究进展

doi:10.6023/cjoc202509010

摘要/Abstract

脱氟反应在化学领域占据着重要地位, 并具有广泛的应用前景. 阐述了脱氟反应的研究进展, 围绕过渡金属催化、光催化、电催化及其他催化体系, 系统介绍了各类脱氟反应过程, 并对部分反应的作用机制与应用前景进行了探讨.

Defluorination reactions hold a crucial position in chemical research and possess broad application prospects. This review summarizes the recent advances in defluorination methodologies, with a focus on representative defluorination processes enabled by transition metal catalysis, photocatalysis, electrocatalysis and other catalytic systems. In addition, the plausible reaction mechanisms and practical applicability of these transformations are discussed.

Key words: defluorination reaction, transition metal catalysis, photocatalysis, electro-catalysis

引用此文

许颖, 杨美琳, 崔大鹏, 于淼, 刘颖杰. 脱氟反应的研究进展[J]. 有机化学, 2026, 46(5): 1962-1983.

Ying Xu, Meilin Yang, Dapeng Cui, Miao Yu, Yingjie Liu. Research Progress on Defluorination Reactions[J]. Chinese Journal of Organic Chemistry, 2026, 46(5): 1962-1983.

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图/表 43

Scheme 1. Rhodium(III)-catalyzed defluorination reaction of perfluorinated aromatics

Scheme 2. Palladium(II)-catalyzed selective defluorinative sulfenylation for the synthesis of fluorovinylthioethers

Scheme 3. Silver(I)-catalyzed defluorination and ring-opening indolylation reaction of siloxodifluorocyclopropanes

Scheme 4. Copper(II)-catalyzed ring-opening defluoridation and alkylation siloxydifluorocyclopropanes

Scheme 5. Palladium(II)-catalyzed defluorinative alkynylation of polyfluoroalkyl ketones with alkynes

Scheme 6. Copper(I)-catalyzed selective defluorinative sulfuration of trifluoropropanamides leading to α-fluorothioacrylamides

Scheme 7. Nickel(0)-catalyzed defluorinative alkylation of C(sp2)—F bonds

Scheme 8. Copper(I) and palladium(0) cocatalyzed defluorinative coupling of gem-difluoroalkenes and acyl chloride

Scheme 9. Cobalt(II)-catalyzed allylic defluorinative cross- electrophile coupling between 1,1-difluoroalkyl halides and α-trifluoromethyl styrenes

Scheme 10. Copper(II)-catalyzed defluorinated halogenated alkylation of non-activated alkenes

Scheme 11. Copper(I)-catalyzed defluoroborylation and hydrodefluorination defluorination of 1-(trifluoromethyl)alkynes

Scheme 12. Chromium(II)-catalyzed defluorinative reductive cross-coupling of acetals with α-trifluoromethyl alkenes

Scheme 13. Silver(I)-catalyzed cascade free radical isonitrile insertion/defluorination cyclization

Scheme 14. Palladium(II)-catalyzed construction of trisubstituted oxazoles from trifluoroalanine derivatives

Scheme 15. Visible light-catalyzed free radical defluoroborylation trifluoromethylolefin

Scheme 16. Visible light-catalyzed defluorinated alkylation of gem-difluoroolefins with 4-alkyl-1,4-dihydropyridines

Scheme 17. Visible light-catalyzed defluoroarylation of trifluoromethylarenes with arylboronic acids

Scheme 18. Visible light-catalyzed defluorinative alkylation or catalyst-free hydroalkylation of gem-difluoroalkenes

Scheme 19. Visible light-induced defluorinative cyclization of α-fluoro-β-enamino esters catalyzed by 4-CzIPN

Scheme 20. Visible light-catalyzed the defluorination and alkylation of trifluoromethylbenzimidazole

Scheme 21. Visible light-catalyzed the defluorination of alkenes from trifluoromethylstyrene

Scheme 22. Photocatalytic defluorination coupling and 5-intra tricyclic synthesis to form 2-fluorobenzofuran

Scheme 23. Visible light-catalyzed C—F bond cleavage for the synthesis of polyfluorinated compound

Scheme 24. Photocatalytic selective defluorination alkylation of dihydroacridine and hydrogenation defluorination reaction

Scheme 25. Photocatalytic reactions of α‑CF3 alkenes with alcohols by controllable mono-defluorination

Scheme 26. Photoinduced cross-coupling of trifluoromethylarenes with heteroarenes via unactivated C(sp3)—F and C(sp2)—H selective cleavage

Scheme 27. Photoredox catalytic defluoroalkylation of gem-difluoroalkene with secondary N‑alkylanilines

Scheme 28. Sulfinate-promoted defluorinative cyclization of polyfluoroalkyl tetralones enabled by photocatalysis

Scheme 29. Synthesis of α-fluoroarylacetic esters and amides via aryl bromides and chlorodifluoroaryl carboxylic acid derivatives

Scheme 30. Y-TCPDA catalyzed chemically selective defluoridation and alkylation reactions

Scheme 31. Electrocatalytic decarboxylation of gem-difluoroolefins in the presence of carbon dioxide

Scheme 32. Electrocatalysis drives the defluorination of gem-difluoroalkene with various alkylating agents

Scheme 33. Ni cathode catalytic synthesis of ArCF2H

Scheme 34. Ni-catalyzed electrochemical N-arylation with versatile aryl electrophiles

Scheme 35. Plausible degradation pathways of 5-FU in the PEC system

Scheme 36. Electrophotocatalytic defluorination of PTFE

Scheme 37. CH3OK-catalyzed the defluoromethoxylation of 2- trifluoromethyl-1,3-alkynes

Scheme 38. Triethylenediamine-catalyzed defluorination of perfluoroalkyl groups

Scheme 39. Cesium(I)-catalyzed defluorination of perfluoroalkyl group

Scheme 40. t-BuOLi-catalyzed defluorination of (trifluoromethyl)alkenes with alcohols

Scheme 41. K3PO4-catalyzed defluorination of trifluoromethylenone

Scheme 42. Defluorination pathways of substances such as 3,3,3-trifluoropropionic acid

Scheme 43. Dehaloperoxidases (DHP)-catalyzed the defluorination of 2,4,6-trifluorophenol

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