N-邻位C(sp3)—H键官能团化合成含氮杂环化合物研究进展

doi:10.6023/cjoc202408019

摘要/Abstract

C(sp³)—H键官能团化是当前有机合成领域的研究热点. N-邻位C(sp³)—H键中的氮原子上孤对电子与邻位碳自由基的单占分子轨道(SOMO)中的电子发生离域后, 降低了C(sp³)—H键的解离能, 有利于引入各种亲核试剂或亲偶极试剂, 通过分子间或分子内亲核环化或偶极环化反应得到结构多样的含氮杂环化合物. 按照N-邻位C(sp³)—H键在不同条件下形成亚胺离子、α-氨基烷基自由基和甲亚胺叶立德等三种中间体进行分类, 综述了近年来N-邻位C(sp³)—H键官能团化合成含氮杂环化合物的研究进展, 阐述了可能经历的化学反应历程, 对其应用前景进行了展望.

关键词: N-邻位C(sp³)—H键, 亚胺离子, α-氨基烷基自由基, 甲亚胺叶立德, 含氮杂环化合物

C(sp³)—H bond functionalization is currently a research hotspot in the field of organic synthesis. The delocalization effect between lone-pair electrons on the nitrogen atom in the N-α-C(sp³)—H bond with the electrons in single occupied molecular orbital (SOMO) of the neighboring carbon radical can reduce the dissociation energy of the C(sp³)—H bond, which facilitates the introduction of various nucleophilic or dipolar reagents into N-α-C(sp³) to provide a variety of nitrogen-contain- ing heterocyclic compounds with diverse structures through intermolecular or intramolecular nucleophilic annulation or dipole cyclization reactions. The research progress in N-α-C(sp³)—H bond functionalization for the synthesis of nitrogen-containing heterocyclic compounds under different conditions through the formation of iminium ions, α-aminoalkyl radicals, and azomethimine ylide intermediates is summarized. The possible reaction processes and their potential applications are discussed.

Key words: N-α-C(sp³)—H bond, iminium ions, α-aminoalkyl radicals, azomethimine ylides, N-heterocycles

引用此文

范玉兰, 邹小颖, 朱小青, 郑绿茵, 郭维. N-邻位C(sp³)—H键官能团化合成含氮杂环化合物研究进展[J]. 有机化学, 2025, 45(4): 1047-1096.

Yulan Fan, Xiaoying Zou, Xiaoqing Zhu, Lüyin Zheng, Wei Guo. Progress in N-α-C(sp³)—H Bond Functionalization for the Synthesis of N-Heterocycles[J]. Chinese Journal of Organic Chemistry, 2025, 45(4): 1047-1096.

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图/表 74

图式1. N-邻位C(sp3)—H键官能团化合成含氮杂环化合物机理

Scheme 1. Possible mechanism for the synthesis of N-heterocycles through N-α-C(sp3)—H bond functionalization

图式2. 铁催化氧化偶联反应合成喹啉类化合物

Scheme 2. Synthesis of substituted quinolines by iron-catalyzed oxidative coupling reactions

图式3. 铜催化氧化 [2＋3]环化合成多取代吡咯烷酮类化合物

Scheme 3. Synthesis of polysubstituted pyrrolidones by copper-catalyzed aerobic oxidative [2＋3] cyclization reactions

图式4. 铜催化多米诺开环和C(sp3)—H官能团化

Scheme 4. Copper-catalyzed domino ring opening and C(sp3)—H functionalization reactions

图式5. 铜催化氧化脱氢[2＋3]环化合成咪唑类化合物

Scheme 5. Synthesis of imidazolidines by copper-catalyzed oxidative dehydrogenative [2＋3] cyclization reactions

图式6. 铜(I)/叔丁基氢过氧化氢促进下合成稠合吡咯类化合物

Scheme 6. Synthesis of pyrrole-fused compounds by copper(I)/tert-butyl hydroperoxide promoted reactions

图式7. 铜催化氧化合成5,6-二氢吡咯并[2,1-a]异喹啉类化合物

Scheme 7. Copper-catalyzed oxidation for the synthesis of 5,6-dihydropyrrolo[2,1-a]isoquinolines

图式8. 铜催化环状胺的a-C(sp3)—H活化合成稠合吡唑衍生物

Scheme 8. Copper(II)-catalyzed-α-C(sp3)—H activation of cyclic amines for the synthesis of fused pyrazole derivatives

图式9. CuBr/NHPI共催化氧化合成5,6-二氢-吡咯并[2,1-a]异喹啉类化合物

Scheme 9. CuBr/NHPI Co-catalyzed aerobic oxidation to access 5,6-dihydro-pyrrolo[2,1-a]isoquinolines

图式10. 自氧化甘氨酸衍生物与烯烃的偶联

Scheme 10. Auto-oxidative coupling of glycine derivatives with olefins

图式11. Br?nsted酸催化合成复杂的喹啉衍生物

Scheme 11. Br?nsted acid catalyzed reaction for the synthesis of complex quinoline derivatives

图式12. 三组分合成嘧啶环类化合物

Scheme 12. Three-component reaction for the synthesis of pyrimidines

图式13. 无过渡金属催化氧化环化合成咪唑并[1,2-a]吲哚衍生物

Scheme 13. Transition-metal-free oxidative annulative coupling reaction for the synthesis of imidazo[1,2-a]indoles

图式14. 氢化物转移引发异喹啉衍生物解构合成3-官能化喹啉

Scheme 14. Hydride transfer-initiated synthesis of 3-functionalized quinolines by deconstruction of isoquinoline derivatives

图式15. 可见光诱导的分子内环化和脱保护基团合成多取代苯并咪唑

Scheme 15. Synthesis of multisubstituted benzimidazoles by visible-light-induced intramolecular cyclization and deprotection

图式16. 可见光诱导的氧化交叉脱氢偶联合成1,3-苯并噁嗪类化合物

Scheme 16. Visible light-induced oxidative cross dehydrogenative coupling reaction for the synthesis of 1,3-benzoxazines

图式17. 可见光诱导氧化脱氢偶联/芳构化串联合成喹啉-2-羧酸酯化合物

Scheme 17. Visible light-induced oxidative dehydrogenative coupling/aromatization tandem reaction for the synthesis of quinoline- 2-carboxylates

图式18. 可见光诱导叔胺的双C(sp3)?H键官能团化

Scheme 18. Visible-light-induced dual C(sp3)?H bond functionalization of tertiary amines

图式19. 可见光促进分子内交叉脱氢偶联合成1,3-噁嗪类化合物

Scheme 19. Visible light-promoted intramolecular cross dehydrogenative coupling approach to 1,3-oxazines

图式20. 可见光催化合成吡咯[2,1-a]异喹啉取代膦酸酯类化合物

Scheme 20. Visible-light photoredox-catalyzed reaction for the synthesis of pyrrolo[1-a]isoquinoline-substituted phosphonates

图式21. 光催化串联开环/氧化胺化合成稠合咪唑衍生物

Scheme 21. Photoredox catalyzed synthesis of fused imidazolidines via tandem ring opening/oxidative amination reactions

图式22. 光催化合成三氟甲基吡咯[2,1-a]异喹啉类化合物

Scheme 22. Synthesis of trifluoromethyl-pyrrolo[2,1-a]isoquinolines with visible light irradiation

图式23. 钴催化氧化环化合成四氢异喹啉衍生物

Scheme 23. Synthesis of tetrahydroquinoline derivatives by cobalt-catalyzed oxidative annulation process

图式24. 催化氧化C(sp3)—H合成喹啉稠合内酯衍生物和2,3-二取代喹啉衍生物

Scheme 24. Construction of quinoline-fused lactones and 2,3-disubstituted quinolines via catalytic aerobic C(sp3)—H oxidation reactions

图式25. 自由基阳离子盐诱导的氧化反应合成喹啉-2-羧酸酯类化合物

Scheme 25. Synthesis of quinoline-2-carboxylate esters through radical cation salt induced aerobic oxidation reactions

图式26. 自由基阳离子盐催化合成喹啉衍生物

Scheme 26. Radical cation salt promoted synthesis of quinoline derivatives

图式27. 铜催化氧化[4＋2]环加成合成多取代的喹啉类化合物

Scheme 27. Synthesis of highly substituted quinolones by copper-catalyzed oxidative [4＋2] cycloaddition reactions

图式28. 铁催化氧化叔苯胺合成喹啉类化合物

Scheme 28. Synthesis of tetrahydroquinolines by iron catalyzed aerobic oxidation of tertiary anilines

图式29. TBPA?＋SbCl－诱导氧化Povarov反应合成氯代喹啉类化合物

Scheme 29. Synthesis of chlorinated quinolones by TBPA?＋SbCl－-initiated oxidative Povarov reactions

图式30. 自由基阳离子盐诱导C(sp3)—H官能团化合成1,4-二氢吡啶类化合物

Scheme 30. Construction of 1,4-dihydropyridines under catalytic radical cation salt-induced C(sp3)—H functionalization reactions

图式31. 自由基阳离子盐促进的C(sp3)—H键氧化合成含1,2-二氢喹啉骨架的化合物

Scheme 31. Radical cation salt-promoted C(sp3)—H bond oxidation for the synthesis of 1,2-dihydroquinoline derivatives

图式32. 自由基阳离子盐催化氧化合成靛红

Scheme 32. Construction of isatin skeleton by radical cation salt initiated aerobic oxidation reactions

图式33. 自由基阳离子盐催化促进C(sp3)—H的氧化合成二氢喹唑啉化合物

Scheme 33. Radical cation salt-induced C(sp3)—H oxidation for the synthesis of dihydroquinazoline derivatives

图式34. Povarov反应合成喹啉-4-羧酸酯类化合物

Scheme 34. Synthesis of quinoline-4-carboxylate esters by Povarov reactions

图式35. 自由基阳离子盐催化合成靛蓝类化合物

Scheme 35. Catalytic radical cation salt-promoted synthesis of isatins

图式36. 分子间[4＋2]/[3＋2]自由基环化合成1,4-二氢喹啉和吡咯并[1,2-α]喹啉类化合物

Scheme 36. Synthesis of 1,4-dihydroquinolines and pyrrolo[1,2-a]quinolines via intermolecular [4＋2]/[3＋2] radical cyclization reactions

图式37. 光催化α-硅基仲胺合成含氮杂环类化合物

Scheme 37. Synthesis of nitrogen heterocycles from α-silyl secondary amines under visible light irradiation

图式38. 可见光催化[3＋2]环加成合成五元环异噁唑烷杂环类化合物

Scheme 38. Synthesis of ?ve-membered ring isoxazolidine heterocycles by visible-light photoredox-catalyzed [3＋2] cycloaddition reactions

图式39. 可见光催化氧化环化合成四氢喹啉类化合物

Scheme 39. Synthesis of tetrahydroquinolines by visible-light-catalyzed aerobic oxidative cyclization reactions

图式40. EDA络合物催化合成四氢喹啉类化合物

Scheme 40. EDA-mediated synthesis of tetrahydroquinolines

图式41. 四氢喹啉类化合物的合成和马来酰亚胺的还原氢化

Scheme 41. Synthesis of tetrahydroquinolines and reductive hydrogenation of maleimides

图式42. 可见光催化分子内偶联环化合成2-芳基吲哚类化合物

Scheme 42. Synthesis of 2-arylindols by visible light catalyzed intramolecular coupling reactions

图式43. 肼基色-2-酮和二氢喹啉-2-酮衍生物的合成

Scheme 43. Synthesis of hydrazide-containing chroman-2-ones and dihydroquinolin-2-ones

图式44. 光催化α-N-C(sp3)—H键活化合成5元杂环γ-氨基酸衍生物

Scheme 44. Synthesis of 5-membered heterocyclic γ-amino acid derivatives by photoredox catalyzed α-N-C(sp3)—H bond activation

图式45. 可见光促进的自由基氧化环化合成菲啶衍生物

Scheme 45. Construction of phenanthridine-6-carboxylates by visible-light-promoted oxidative radical cyclization reactions

图式46. 光促进的N-杂环卡宾催化四氢异喹啉-乙醛分子内交叉脱氢偶联

Scheme 46. Photopromoted N-heterocyclic carbene catalyzed intramolecular cross dehydrogenative coupling of tetrahydroisoquinoline-tethered aldehydes

图式47. 可见光催化氧化Povarov反应合成吡咯并[3,4-c]喹啉-1,3-二酮类化合物

Scheme 47. Synthesis of pyrrolo[3,4-c]quinoline-1,3-diones by visible light catalyzed oxidative Povarov reactions

图式48. Rh2(cap)4催化氧化合成3,4-二氢吡咯并[2,1-a]异喹啉类化合物

Scheme 48. Synthesis of 3,4-dihydropyrrolo[2,1-a]isoquinolines by Rh2(cap)4-catalyzed oxidation reactions

图式49. 铁催化合成吡咯并[2,1-a]异喹啉类化合物

Scheme 49. Iron-catalyzed synthesis of pyrrolo[2,1-a]isoquinolines

图式50. 金催化剂介导下的三组分反应合成含吡咯烷骨架的化合物

Scheme 50. Gold catalyst mediated three-component domino process for the synthesis of pyrrolizine skeletons

图式51. 醋酸铜促进的氧化[3＋2]环化合成中氮茚类化合物

Scheme 51. Synthesis of indolizines by copper-mediated oxidative [3＋2]-annulation reactions

图式52. 铜(Ⅱ)催化氧化[3＋2]环化合成稠合氮杂环类化合物

Scheme 52. Synthesis of N-fused heterocycles via Cu(II)-mediated oxidative [3＋2]-annulation reactions

图式53. 铜催化环化合成具有苯并[7,8]吲嗪骨架的亚胺化合物和苯并[7,8]吲哚并[1,2-c]喹啉类化合物

Scheme 53. Synthesis of imines with a benzo[7,8]indolizine core and benzo[7,8]indolizino[2-c]quinolines via copper-catalyzed annulation reactions

图式54. I2/H2O2催化体系合成吡咯并[2,1-a]异喹啉类化合物

Scheme 54. Synthesis of pyrrolo[2,1-a]isoquinolines using a I2/H2O2 catalytic system

图式55. KI/TBHP催化合成吡咯并[2,1-a]异喹啉类化合物

Scheme 55. Synthesis of pyrrolo[2,1-a]isoquinolines using a KI/TBHP catalytic system

图式56. 碱促进的分子间环化合成吡咯并[2,1-a]异喹啉类化合物

Scheme 56. Synthesis of pyrrolo[2,1-a]isoquinolines by base-promoted intermolecular cyclization reactions

图式57. 分子碘诱导1,3-偶极环加成/氧化芳构化合成2-取代苯并[f]异吲哚-1,3-二甲酸酯类化合物

Scheme 57. Synthesis of 2-substituted benzo[f]isoindole-1,3-dicarboxylates by molecular iodine induced/1,3-dipolar cycloaddition/oxi- dative aromatization sequence

图式58. 乙酸促进四氢异喹啉和2-烷基喹啉-3-甲醛的氧化还原环化

Scheme 58. Acetic acid promoted redox annulations of 1,2,3,4-tetrahydroisoquinoline with 2-alkylquinoline-3-carbaldehydes

图式59. 苯甲酸促进分子间[3＋2]环加成合成吡咯并[2,1-a]异喹啉类化合物

Scheme 59. Synthesis of pyrrolo[2,1-a]isoquinolines by benzoic acid-promoted intermolecular [3＋2] cycloaddition reactions

图式60. 酸介导的分子间[3＋2]环加成反应合成吡咯并[2,1-a]异喹啉类化合物

Scheme 60. Acid-mediated intermolecular [3＋2] cycloaddition toward pyrrolo[2,1-a]isoquinolines

图式61. 碱催化合成吡咯并[2,1-a]异喹啉类化合物和稠合的五环香豆素类化合物

Scheme 61. Synthesis of pyrrolo[2,1-a]isoquinoline and coumarin-fused pentacyclic derivatives by base-catalyzed annulation reactions

图式62. [3＋2] 1,3-偶极环加成合成稠合三环咪唑啉衍生物

Scheme 62. Synthesis of tricyclic imidazolines derivatives via [3＋2] 1,3-dipolar cycloaddition reactions

图式63. 1,3-偶极环加成合成2,3-二氢吡唑、2,3-二氢异噁唑和中氮杂环类化合物

Scheme 63. Synthesis of 2,3-dihydropyrazoles, 2,3-dihydroisoxazoles, and indolizines by 1,3-dipolar cycloaddition reactions

图式64. 碱介导的1,3-偶极环化合成中氮茚衍生物

Scheme 64. Synthesis of indolizine derivatives by base-mediated 1,3-dipolar cycloaddition reactions

图式65. 吡啶盐和溴二氟乙酸乙酯合成中氮茚

Scheme 65. Synthesis of indolizines from pyridinium salts and ethyl bromodifluoroacetate

图式66. [3＋2]环加成合成吲哚嗪和吡唑并[1,5-a]吡啶类化合物

Scheme 66. Synthesis of indolizines and pyrazolo[5-a]pyridines via [3＋2]-cycloaddition reactions

图式67. 氧化[3＋2]环化合成2-氟中氮茚类化合物

Scheme 67. Synthesis of 2-fluoroindolizines by oxidative [3＋2] annulation reactions

图式68. 甲亚胺叶立德与缺电子烯烃的迈克尔加成/消除串联反应

Scheme 68. Tandem Michael addition/elimination of pyridinium ylides with electron-deficient alkenes

图式69. 无过渡金属催化下氨基酸衍生物的扩环合成氮杂?类化合物

Scheme 69. Synthesis of azepines via transition-metal-free catalyzed ring expansion of amino acid derivatives

图式70. 电化学催化合成N-杂多环化合物

Scheme 70. Electrochemical synthesis of polycyclic N-heterocycles

图式71. 电催化[3＋2]环加成合成含氮化合物

Scheme 71. Electrochemical synthesis of N-heterocycles via [3＋2] cycloaddition reactions

图式72. 可见光下叶绿素催化环加成反应合成吡咯并[2,1-a]异喹啉化合物

Scheme 72. Synthesis of pyrrolo[2,1-a]isoquinolines by chlorophyll-catalyzed cycloaddition reaction under visible light

图式73. 可见光催化[3＋2]环化反应合成咪唑并[2,1-a]异喹啉类化合物

Scheme 73. Synthesis of imidazo[2,1-a]isoquinolines by visible-light-catalyzed [3＋2] annulation reactions

图式74. 可见光介导的去芳香化扩环合成氮杂?类化合物

Scheme 74. Synthesis of azepines by visible-light-mediated dearomative ring expansion

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N-邻位C(sp³)—H键官能团化合成含氮杂环化合物研究进展

Progress in N-α-C(sp³)—H Bond Functionalization for the Synthesis of N-Heterocycles

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