硫氟交换点击反应合成方法学研究进展

doi:10.6023/cjoc202512025

摘要/Abstract

硫(Ⅵ)氟交换(Sulfur(Ⅵ) fluoride exchange, 简称SuFEx)反应是Sharpless等发展的新一代点击化学. 经过十几年的发展, SuFEx反应在合成化学、材料科学、化学生物学和药物发现等诸多领域获得广泛应用. 到目前为止, 化学家已经合成出了多个SuFEx链接子, 并通过与不同亲核试剂的SuFEx反应实现了磺酰胺、磺酸酯等多种重要含硫化合物的高效合成. 与S(VI)—Cl键相比, S(VI)—F键具有高键离解能和化学稳定性, 因此SuFEx反应往往需要特定的反应条件和催化剂才能发生. 概述了不同链接子参与的SuFEx反应进展, 着重对其反应方法学进行了总结.

关键词: 硫(Ⅵ)氟交换, 点击反应, SuFEx链接子, 含硫化合物

Sulfur(VI) fluoride exchange (SuFEx) is new generation of click chemistry developed by Sharpless and co-workers. Over the past decade, SuFEx has found broad applications in synthetic chemistry, materials science, chemical biology, and drug discovery. Chemists have prepared a variety of SuFEx linkers, which can efficiently undergo SuFEx reactions with different nucleophiles to afford a diverse of highly valued sulfur-containing compounds such as sulfonamides, sulfonates and so on. Compared to S(VI)—Cl bond, S(VI)—F bond has higher bond-dissociation energy and chemical stability. Consequently, SuFEx reactions usually require specific reaction conditions and catalysts. This review summarizes recent advances in SuFEx reactions involving different linkers, with an emphasis on their methodological development.

Key words: sulfur (VI) fluoride exchange, click reaction, SuFEx linker, sulfur-containing compounds

引用此文

迪力非热古丽•买纳洪, 张启超, 张放, 何林, 蔡志华, 杜广芬. 硫氟交换点击反应合成方法学研究进展[J]. 有机化学, 2026, 46(8): 2988-3011.

Dilfiragul Mangnahun, Qichao Zhang, Fang Zhang, Lin He, Zhihua Cai, Guangfen Du. Recent Advances in Synthetic Methodology of Sulfur(VI) Fluoride Exchange Click Reactions[J]. Chinese Journal of Organic Chemistry, 2026, 46(8): 2988-3011.

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图/表 55

图式1. 点击反应及SuFEx链接子

Scheme 1. Click reaction and SuFEx linkers

图式2. (A) SO2F2与酚的反应; (B) SO2F2与杂环酚的反应

Scheme 2. (A) Reaction of SO2F2 with phenols; (B) Reaction of SO2F2 with heterocyclic phenols

图式3. 加速的SuFEx反应

Scheme 3. Accelerated SuFEx reaction

图式4. SO2F2与胺类化合物的反应

Scheme 4. Reaction of SO2F2 with amines

图式5. SO2F2参与的三组分反应

Scheme 5. Three-component reaction involving SO2F2

图式6. SO2F2与盐酸胍盐的反应

Scheme 6. Reaction of SO2F2 with guanidine hydrochlorides

图式7. SuFEx-IT的合成及其与酚类和胺类化合物的反应

Scheme 7. Synthesis of SuFEx-IT and their reactions with phenols and amines

图式8. AISF的合成及其与酚和环状二级胺的反应

Scheme 8. Synthesis of AISF and its reactions with phenols and cyclic secondary amines

图式9. BTSF, BDSF参与的SuFEx反应

Scheme 9. SuFEx reactions involving BTSF and BDSF

图式10. 氟磺酰基叠氮化物的合成及其应用

Scheme 10. Synthesis and applications of fluorosulfonyl azides

图式11. 新型硫(Ⅵ)氟化物SIFs参与的反应

Scheme 11. Reaction involving novel sulfur(VI) fluorides SIFs

图式12. 磺酰氟与氧亲核试剂的反应

Scheme 12. Reaction of sulfonyl fluorides with oxygen nucleophiles

图式13. ChB活化的SuFEx反应

Scheme 13. ChB-activated SuFEx reaction

图式14. 加速的SuFEx反应

Scheme 14. Accelarated SuFEx reaction

图式15. 氟代磺酸酯与糖类和氨基酸的反应

Scheme 15. Rreaction of aryl fluorosulfates with sugar or amino acid

图式16. NHC催化的SuFEx反应

Scheme 16. NHC-catalyzed SuFEx reaction

图式17. 双氟盐催化的SuFEx聚合反应

Scheme 17. Bifluoride salt catalyzed SuFEx polymerization

图式18. 磺酰氟与胺的SuFEx反应

Scheme 18. SuFEx reaction of sulfonyl fluorides with amines

图式19. 通过SuFEx反应合成磺酰胺类化合物

Scheme 19. Synthesis of sulfonamides via SuFEx reaction

图式20. HOBt催化磺酰氟与氟代磺酸酯和胺的SuFEx反应

Scheme 20. HOBt-catalyzed SuFEx reaction of sulfonyl fluorides with fluorosulfates and amines

图式21. NHC催化胺的SuFEx反应

Scheme 21. NHC-catalyzed SuFEx reaction of amines

图式22. 气态CF3SO2F参与的SuFEx反应

Scheme 22. SuFEx reaction involving gaseous CF3SO2F

图式23. NMI作用下合成磺酰胺类化合物

Scheme 23. Synthesis of sulfonamides under NMI mediation

图式24. 具有SuFEx活性底物参与的Friedel-Crafts环化反应

Scheme 24. Friedel-Crafts cyclizations involving substrates with SuFEx reactivity

图式25. SOF4与胺类化合物的SuFEx反应

Scheme 25. SuFEx reaction of SOF4 with amines

图式26. (A)亚砜亚胺氟化物的合成; (B)亚砜亚胺二氟化物与硅醚的SuFEx反应; (C) SO2F2和SOF4的选择性SuFEx反应

Scheme 26. (A) Synthesis of sulfoximine fluorides; (B) SuFEx reaction of sulfoximine difluorides with silyl ethers; (C) Selective SuFEx reactions of SO2F2 and SOF4

图式27. 亚砜亚胺二氟化物参与的SuFEx反应

Scheme 27. SuFEx reactions involving sulfoximine difluorides

图式28. 砜亚胺类衍生物与氧亲核试剂的SuFEx反应

Scheme 28. SuFEx reactions of sulfonimidoyl derivatives with oxygen nucleophiles

图式29. 亚砜亚胺单氟化物与炔基硅醚的C-SuFEx反应

Scheme 29. C-SuFEx reaction of sulfilimine monofluorides with alkynyl silyl ethers

图式30. 亚砜亚胺单氟化物与非环化烯烃的C-SuFEx反应

Scheme 30. C-SuFEx reaction of sulfilimine monofluorides with acyclic alkenes

图式31. 亚砜亚胺单氟化物与烯丙基硅的C-SuFEx反应

Scheme 31. C-SuFEx reactions of fluorinated sulfoximines with allylsilanes

图式32. TMSOTf催化的C-SuFEx反应

Scheme 32. TMSOTf-catalyzed C-SuFEx reaction

图式33. 亚砜亚胺氟化物在合成高分子化合物方面的应用

Scheme 33. Applications of fluorinated sulfonimidates in the synthesis of polymeric compound

图式34. 从稳定的N-Boc-亚砜胺盐制备高对映体亚砜亚胺衍生物

Scheme 34. Highly enantioenriched sulfoximines prepared from bench-stable N-Boc-sulfinylamine salts

图式35. 利用手性S(Ⅵ)-t-BuSF合成光学活性亚砜亚胺衍生物

Scheme 35. Optically active sulfoximine derivatives synthesized from chiral S(Ⅵ)-t-Bu

图式36. 不对称三维硫氟交换(3D-SuFEx)反应

Scheme 36. Asymmetric 3D sulfur-fluoride exchange (3D-SuFEx)

图式37. 手性SuFEx链接子SIFs的合成及其应用

Scheme 37. Synthesis and applications of chiral SuFEx linkers SIFs

图式38. NaHF2促进的S(VI)中心F/Cl不对称交换反应

Scheme 38. NaHF2 promoted asymmetric F/Cl exchange reaction at the S(VI) center

图式39. 通过“水相反应”制备公斤级别ESF

Scheme 39. Kilogram-scale synthesis of ESF via an aqueous- phase reaction

图式40. ESF参与的Heck反应

Scheme 40. Heck reaction involving ESF

图式41. β-芳基乙烯基磺酰氟与胺的SuFEx反应

Scheme 41. SuFEx reaction of β-aryl vinylsulfonyl fluorides with amines

图式42. β-芳基乙烯基磺酰氟与酮进行的SuFEx反应

Scheme 42. SuFEx reaction of β-aryl vinylsulfonyl fluorides with ketones

图式43. 通过SuFEx反应高效合成内磺酸酯

Scheme 43. Efficient synthesis of sultones via SuFEx reaction

图式44. BESF的合成及其应用

Scheme 44. Synthesis and applications of BESF

图式45. BESF在合成SuFEx活性底物方面的应用

Scheme 45. Applications of ESF in the synthesis of SuFExable substrates

图式46. 通过BESF合成SuFEx链接子

Scheme 46. SuFEx linkers prepared from BESF

图式47. BDF的合成及其在合成SuFEx活性底物方面的应用

Scheme 47. Synthesis of BDF and its application in preparing SuFEx-active substrate

图式48. β-芳基乙烯基磺酰氟参与构建三芳基苯化合物

Scheme 48. Construction of triphenylbenzenes via β-aryl vinylsulfonyl fluorides

图式49. 经由β-芳基乙烯基磺酰氟串联反应构建环己(戊)烯类化合物

Scheme 49. Construction of cyclohexenes and cyclopentenes via tandem reaction of β-aryl vinylsulfonyl fluorides

图式50. β-芳基乙烯基磺酰氟与o-羟基偶氮甲碱叶立德的环加成反应

Scheme 50. Cycloaddition of β-aryl vinylsulfonyl fluorides with o-hydroxy azomethine ylides

图式51. 以β-芳基乙烯基磺酰氟合成α-芳基吡咯烷

Scheme 51. Synthesis of α-arylpyrrolidines with β-aryl vinylsulfonyl fluorides

图式52. β-芳基乙烯基磺酰氟与吲哚酮和苯并呋喃酮的SuFEx反应

Scheme 52. SuFEx reaction of β-aryl vinylsulfonyl fluorides with oxindoles and benzofuranones

图式53. 硅胶促进的SuFEx环化反应

Scheme 53. Silica-promoted SuFEx cyclization

图式54. SASF的合成及其参与的反应

Scheme 54. Synthesis of SASF and its reactions

图式55. 利用SASF合成新型可点击噻唑类化合物

Scheme 55. Synthesis of novel clickable thiazoles using SASF

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