N-磺酰基酮亚胺的C—H官能团化研究进展

doi:10.6023/cjoc202512014

摘要/Abstract

N-磺酰基酮亚胺因其独特的结构、显著的生物活性和潜在的药用价值而受到广泛关注. N-磺酰基酮亚胺作为多功能的合成结构单元, 在合成化学中具有广泛的应用, 用于构建复杂的手性杂环. 总结了过去5年N-磺酰基酮酰亚胺官能化的最新进展. 根据所涉及的不同反应类型, 对代表性实例和详细的反应机理进行了分类和详细讨论.

关键词: N-磺酰基酮亚胺, 烷基化, 环化, 胺化, 酰化

N-Sulfonyl ketimines have attracted great attention due to unique structure, significant biological activities and potential medicinal value. As versatile synthetic building blocks, N-sulfonyl ketimines have wide applications in synthetic chemistry, for the construction of complex and chiral heterocycles. In this review, recent advances in N-sulfonylketimide functionalization over the past five years are summarized. Based on the different reaction types involved, representative examples and detailed reaction mechanisms are categorized and discussed in detail.

Key words: N-sulfonyl ketimine, alkylation, annulation, amination, acylation

引用此文

尚金凤, 季红涛, 黄佳垚, 李荣强. N-磺酰基酮亚胺的C—H官能团化研究进展[J]. 有机化学, 2026, 46(6): 2275-2309.

Jinfeng Shang, Hongtao Ji, Jiayao Huang, Rongqiang Li. Recent Progress in C—H Functionalization of N-Sulfonyl Ketimines[J]. Chinese Journal of Organic Chemistry, 2026, 46(6): 2275-2309.

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图/表 29

Figure 1. Representative biologically active N-sulfonyl keti- mines moieties

Scheme 1. Synthesis of N-sulfonyl ketimines

Figure 2. C—H functionalization of N-sulfonyl ketimines

Scheme 2. Silver-catalyzed decarboxylative C—H functionalization of N-sulfonyl ketimines with aliphatic carboxylic acids

Scheme 3. Ag-catalyzed ring-opening for C—H functionalization of N-sulfonyl ketimines with tertiary cycloalkanols

Scheme 4. Solvent-controlled silver catalyzed radical transformation of α-imino-oxy acids with N-sulfonyl ketimines

Scheme 5. Silver-catalyzed oxidative ring-opening of cyclic aliphatic amines for C—H alkylation of N-sulfonyl ketimines

Scheme 6. Photoinduced decatungstate-catalyzed direct coupling of cycloalkanes and N-sulfonyl ketimines

Scheme 7. External photocatalyst-free C—H alkylation of N- sulfonyl ketimines with alkanes

Scheme 8. Nd@C3N4-photoredox/chlorine dual catalyzed alkylation

Scheme 9. CeCl3-catalyzed C—H alkylation of N-sulfonyl ketimines with alkanes and ether via photoinduced LMCT chlorine-radical and air

Scheme 10. Catalyst-free, air-mediated C(sp2)—H alkylation of N-sulfonyl ketimines with alkylboronic acids

Scheme 11. Photoinduced metal- and photosensitizer-free decarbonylative C—H alkylation

Scheme 12. Iron catalyzed alkylation of N-sulfonyl ketimines with olefins via metal hydride atom transfer

Scheme 13. Perovskite catalyzed annulation reaction of N-sulfonyl ketimines

Scheme 14. Oxygen-doped carbon nitride catalyzed decarboxylative annulation reactions

Scheme 15. Ferrocene-mediated photocatalytic annulation of N-sulfonyl ketimines on polycrystalline WSe2

Scheme 16. H-bond promoted NPh3-mediated SrTiO3-photocatalyzed cascade decarboxylative coupling/annulation of benzo[d]isothiazole 1,1-dioxides

Scheme 17. Eosin Y catalyzed homogeneous cyclization of cyclic N-sulfonyl ketimines

Scheme 18. EtOH-catalyzed electrosynthesis of imidazolidine-fused sulfamidates

Scheme 19. Supporting-electrolyte-free electrochemical [2+2+1] annulation of five-membered N-sulfonyl ketimines

Scheme 20. Electro-catalyzed, solvent-controlled divergent decarboxylative annulation and hydroaminomethylation of N-sulfonyl ketimines

Scheme 21. Organocatalytic asymmetric [3+2]-annulations of γ-sulfonamido/γ-hydroxy-α,β-unsaturated ketones with N-sulfonyl ketimines: synthesis of chiral polyheterotricyclic imidazolidines and oxazolidines

Scheme 22. An eosin Y-catalyzed C(sp2)—N cross coupling reaction of N-sulfonyl ketimines with cyclic aliphatic amines

Scheme 23. Electrochemically driven oxidative C—H/N—H cross-coupling reactions of N-sulfonyl ketimines with primary anilines and secondar amines

Scheme 24. Potassium-modified carbon nitride photocatalyzed-aminoacylation of N-sulfonyl ketimines

Scheme 25. Catalyst-free direct ring-opening of N-sulfonyl ketimines with aliphatic primary amines to construct o-hydroxy schiff bases

Scheme 26. Cu(OAc)2/DABCO-mediated domino reaction of N-sulfonyl ketimines with vinyl malononitriles to access 6-hydroxyaryl- 2-aminonicotinonitriles

Scheme 27. Assembly of nitrated isoxazoles using benzoxathiazine-2,2-dioxides as C1 synthons

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