基于氢原子迁移(HAT)过程的胺类化合物选择性C—H键转化反应研究进展

doi:10.6023/cjoc202503010

摘要/Abstract

烷基胺类化合物是重要的有机分子, 对其不同位点的碳氢键进行精准转化是当前有机合成化学的研究热点之一. 氢原子迁移(HAT)作为一种温和可控的碳氢键活化策略, 近些年来受到了极高的关注并被广泛用于胺类分子的选择性碳氢键转化. 通过分子间或分子内HAT过程可以精准导向攫取胺类分子中特定位点的氢原子并实现后续转化, 为复杂胺类功能分子的高效构筑提供了全新的合成思路. 总结了基于上述策略的胺类分子碳氢键选择性官能团化反应进展, 对其中的区域、化学和立体选择性调控机制以及反应机理进行评述, 分析存在的局限性以及展望未来研究方向．

关键词: 氢原子转移, 胺, C—H键官能团化, 区域选择性, 立体选择性, 自由基

Aliphatic amines are pivotal organic molecules, and therefore the precise C—H transformation of amines at distinct sites has long been a research focus in organic synthesis. Hydrogen atom transfer (HAT), recognized as a mild and controllable strategy for C—H activation, has attracted considerable attention in recent years and is extensively employed for the selective C—H transformation of amine molecules. By leveraging intermolecular or intramolecular HAT processes, it becomes feasible to precisely abstract C—H bonds at specific sites within amine molecules and facilitate subsequent transformations, providing novel synthetic pathways for the efficient construction of complex functional amine molecules. The recent advances in the selective functionalization of C—H bonds of amine molecules using the aforementioned strategy are comprehensively summarized. A review is conducted on the regio-, chemo-, and stereoselective regulatory mechanisms, as well as the reaction mechanisms involved. In addition, the limitation in this research field is analyzed and the outlook of this area is also prospected.

Key words: hydrogen atom transfer, amine, C—H functionalization, regioselectivity, stereoselectivity, radical

引用此文

李欢乐, 潘其, 娄绍杰, 毛羊杰, 许丹倩. 基于氢原子迁移(HAT)过程的胺类化合物选择性C—H键转化反应研究进展[J]. 有机化学, 2025, 45(9): 3213-3243.

Huanle Li, Qi Pan, Shaojie Lou, Yangjie Mao, Danqian Xu. Recent Advances in Selective C—H Bond Functionalization of Amines Through Hydrogen Atom Transfer (HAT) Process[J]. Chinese Journal of Organic Chemistry, 2025, 45(9): 3213-3243.

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图/表 45

图式1. 胺类化合物C—H键选择性官能团化策略

Scheme 1. Strategies for selective functionalization of C—H bonds in amines

图式2. 1,5-HAT实现胺类化合物α位C—H键醚化

Scheme 2. α-C—H Etherification of amines via 1,5-HAT

图式3. 1,5-HAT介导的胺类化合物α位C—H键硼化

Scheme 3. α-C—H borylation of amines via 1,5-HAT

图式4. 1,5-HAT介导的胺类化合物α位C—H键磷酸化

Scheme 4. α-C—H phosphonylation of amines via 1,5-HAT

图式5. 环胺化合物α-C—H键对映选择性炔基化

Scheme 5. Enantioselective α-C—H alkynylation of cyclic amines

图式6. 胺类化合物α-C—H键硅基化和烯基化

Scheme 6. α-C—H silylation and alkenylation of amines

图式7. 光/钯催化哌啶衍生物的不对称烯丙基烷基化

Scheme 7. Photoinduced Pd-catalyzed asymmetric allylic alkylation of piperidine scaffolds

图式8. 基于1,4-HAT的铜催化α-C—H键官能团化

Scheme 8. Cu-catalyzed α-C—H functionalization via 1,4-HAT

图式9. 金属自由基催化分子内不对称烷基化合成吲哚

Scheme 9. Synthesis of indoles through asymmetric alkylation catalyzed by MRC

图式10. 基于碱辅助1,2-HAT的胺基α-C—H键烷基化

Scheme 10. α-C—H Alkylation of amines via base-assisted 1,2-HAT

图式11. 碱辅助1,2-HAT介导的α-C—H键偕二氟烯丙基化

Scheme 11. gem-Difluoroallylation of α-C—H via base-assisted 1,2-HAT

图式12. 基于极性匹配的镍催化、光氧化还原和HAT的三组分催化C(sp3)—H交叉偶联烷基化

Scheme 12. C(sp3)—H alkylation via polarity-match-based cross-coupling combined with photoredox, nickel and HAT catalysis

图式13. 光催化伯胺衍生物α-C(sp3)—H烷基化

Scheme 13. Photoredox-catalyzed α-C(sp3)—H alkylation of primary amine derivatives

图式14. 光催化胺基α-C(sp3)—H甲基化

Scheme 14. Photoredox-catalyzed α-C(sp3)—H methylation of amines

图式15. 胺基α-C(sp3)—H键官能团化

Scheme 15. α-C(sp3)—H Functionalization of amines

图式16. 胺基α-C(sp3)—H键对映选择性烷基化

Scheme 16. Enantioselective α-C(sp3)—H alkylation of amines

图式17. 脂肪胺类化合物中的C—H键

Scheme 17. Diverse C—H bonds in aliphatic amines

图式18. 可逆HAT催化的叔胺α‑C—H键选择性烷基化

Scheme 18. Site-selective α‑C—H alkylation of trialkylamines via reversible HAT catalysis

图式19. HAT催化自由基介导的烷基仲胺α-C(sp3)—H键位置选择性迁移芳基化

Scheme 19. Site-selective α-C(sp3)—H arylation of dialkylamines via HAT catalysis enabled radical aryl migration

图式20. 金属/光氧化还原催化的N-烷基苯并酰胺的对映选择性C—H键官能团化

Scheme 20. Metallaphotoredox-mediated enantioselective C—H functionalization of N-alkyl benzamides

图式21. 光/镍协同催化含氮杂环的位置和对映选择性酰基化

Scheme 21. Site- and enantioselective acylation of N-heterocycles by cooperative Ni/photoredox catalysis

图式22. 药物分子后期甲基化

Scheme 22. Late-stage C(sp3)—H methylation of drug molecules

图式23. 基于Co(II)金属自由基催化的C(sp3)—H键胺化

Scheme 23. C(sp3)—H amination based on Co(II)-MRC catalysis

图式24. C(sp3)—H键的对映选择性分子内胺化

Scheme 24. Enantioselective intramolecular amination of C(sp3)—H bonds

图式25. 光催化胺类化合物β-C(sp3)—H官能团化

Scheme 25. Photocatalysis β-C(sp3)—H functionalization of amines

图式26. 磺酰胺导向自由基介导的脂肪胺γ-C—H键卤化

Scheme 26. Sulfamide-directed radical-mediated γ-C—H halogenation of amines

图式27. Co(II)催化磺酰胺叠氮化物分子内不对称C(sp3)—H键胺化

Scheme 27. Co(II)-catalyzed enantioselective C(sp3)—H intramolecular amination of sulfamoyl azides

图式28. 三重HAT促进的胺类化合物γ-C—H键官能团化

Scheme 28. γ-C—H functionalization of amines via triple HAT

图式29. 光驱动三元催化脂肪胺γ-C—H键官能团化

Scheme 29. γ-C—H Functionalization of amines via light-driven triple catalysis

图式30. 磺酰基导向的1,6-HAT构建γ-C(sp3)—N键

Scheme 30. Sulfonyl directed γ-C(sp3)—N construction via 1,6-HAT

图式31. 可见光促进的δ-C(sp3)—H键氯化和胺化

Scheme 31. Visible-light-promoted δ-C(sp3)—H chlorination and amidation

图式32. 锰介导的胺基δ位氯化

Scheme 32. Manganese-mediated δ-chlorination of amines

图式33. 铜催化δ-C(sp3)—H键二氟甲基化

Scheme 33. Copper-catalyzed difluoromethylation of δ-C(sp3)—H bonds

图式34. 铜催化酰胺和磺酰胺δ-C(sp3)—H键官能团化

Scheme 34. Copper-catalyzed δ-C(sp3)—H functionalization of carboxamides and sulfonamides

图式35. 铜催化远端C(sp3)—H键不对称氰基化

Scheme 35. Copper-catalyzed enantioselective cyanation of remote C(sp3)—H bonds

图式36. 铜催化δ-C(sp3)—H键不对称炔基化

Scheme 36. Copper-catalyzed enantioselective alkynylation of δ-C(sp3)—H bonds

图式37. N-氟代酰胺导向的远端C(sp3)—H键不对称烷基化

Scheme 37. N‑Fluoroamide directed asymmetric alkylation of remote C(sp3)—H bonds

图式38. 酰胺自由基导向的δ-C(sp3)—H键烷基化

Scheme 38. Amidyl radical directed alkylation of δ-C(sp3)—H bonds

图式39. 氮氧键介导的胺基δ-C(sp3)—H键官能团化

Scheme 39. N—O bond mediated δ-C(sp3)—H functionalization of amines

图式40. 铜催化δ-C(sp3)—H键不对称氰基化

Scheme 40. Copper-catalyzed enantioselective cyanation of δ-C(sp3)—H bonds

图式41. 氮硫键介导的胺基δ-C(sp3)—H键官能团化

Scheme 41. N—S bond mediated δ-C(sp3)—H functionalization of amines

图式42. 光催化酰胺导向δ-C—H键烷基化

Scheme 42. Photoredox-catalyzed amide-directed alkylation of δ-C—H bonds

图式43. δ-C(sp3)—H键选择性氘化

Scheme 43. Selective deuteration of δ-C(sp3)—H bonds

图式44. 电子/质子转移促进的δ-C(sp3)—H键杂芳基化

Scheme 44. δ-C(sp3)—H heteroarylation enabled by sequential electron/proton transfer

图式45. 电化学促进的δ-C(sp3)—H硫氰化

Scheme 45. Electrochemical δ-C(sp3)—H thiocyanation

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