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

doi:10.6023/cjoc202408019

Abstract

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

Cite this article

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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Fig. & Tab. 74

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Scheme 26. Radical cation salt promoted synthesis of quinoline derivatives

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

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

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

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

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

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

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

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

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

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

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

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

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

Scheme 40. EDA-mediated synthesis of tetrahydroquinolines

Scheme 41. Synthesis of tetrahydroquinolines and reductive hydrogenation of maleimides

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Scheme 70. Electrochemical synthesis of polycyclic N-heterocycles

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

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

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

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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N-邻位C(sp3)—H键官能团化合成含氮杂环化合物研究进展