基于电化学方法构建碳-氮键的最新研究进展

doi:10.6023/cjoc202012013

摘要/Abstract

C—N键广泛存在于药物、天然产物以及功能材料中, 它的构建是有机合成化学的重要研究方向之一. 近年来,随着有机电化学的深入发展, 以有机电化学作为绿色合成手段, 高效地构建C—N键受到了合成化学家的广泛关注. 综述了从2015年至今有机电化学在构建C—N键领域所取得的研究进展, 对反应的条件和机理进行了总结, 并对该领域所面临的挑战及发展方向进行了展望与探讨, 希望能对从事该领域研究的学者以及相关人员提供参考.

关键词: 有机电化学, C—N键, 绿色化学

C—N bonds are widely existed in drugs, natural products, and functional materials. Thus, the construction of C—N bonds is one of the most important research areas in academia and industry. Recently, the renaissance in organic electrochemistry has promoted the electrochemical C—N bond formations to be a special branch of organic synthesis. The most recent advances in the electrochemical C—N bond formations since 2015 are summarized. The reaction mechanisms of these transformations are discussed, and the challenges and future directions of this important filed are included. We hope that this review can give references to the researchers, graduate students and other related people.

Key words: organic electrochemistry, carbon-nitrogen bond, green chemistry

引用此文

蒙泽银, 冯承涛, 徐坤. 基于电化学方法构建碳-氮键的最新研究进展[J]. 有机化学, 2021, 41(7): 2535-2570.

Zeyin Meng, Chengtao Feng, Kun Xu. Recent Advances in the Electrochemical Formation of Carbon-Nitrogen Bonds[J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2535-2570.

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图/表 67

图式1. 2'-氨基苯乙酮的电化学分子内氧化环化反应

Scheme 1. Electrochemically oxidative intramolecular cyclization of 2'-amino-acetophenones

图式2. 电化学苄基C(sp3)—H胺化反应

Scheme 2. Electrochemical benzylic C(sp3)—H amination

图式3. 电氧化诱导的分子内C(sp3)—H胺化反应

Scheme 3. Electrochemically induced oxidative intramolecular C(sp3)—H amination

图式4. 电化学合成反式-2,3-二取代氮杂环丙烷

Scheme 4. Electrochemical synthesis of trans-2,3-disubstituted aziridines

图式5. 电化学合成β-烯胺酮

Scheme 5. Electrochemical synthesis of β-enaminones

图式6. 电化学合成α-甲烯胺酮

Scheme 6. Electrochemical synthesis of α-enaminones

图式7. 电化学氧化条件下C(sp3)—H与唑类化合物的胺化反应

Scheme 7. Electro-oxidative C(sp3)—H amination with azoles

图式8. 内酰胺与唑的电化学脱氢偶联反应

Scheme 8. Electrochemical oxidative azolation of lactams

图式9. 黄嘌呤与氧杂蒽与N-烷氧基酰胺的分子间电化学C(sp3)—H/N—H交叉偶联反应

Scheme 9. Electrochemically intermolecular C(sp3)—H/N—H cross-coupling of xanthenes with N-alkoxyamide

图式10. 甲基N-杂芳烃与胺的电化学C(sp3)—H/N—H偶联反应

Scheme 10. Electrochemical intermolecular C(sp3)—H/N—H coupling of methyl N?heteroaromatics with amines

图式11. 电化学合成偕二胺

Scheme 11. Electrochemical synthesis of gem-diamines

图式12. N-烯丙基酰胺与1,3-二羰基化合物的电化学氧化环化反应

Scheme 12. Electrooxidative annulation of N-allyl amides with 1,3-dicarbonyl compounds

图式13. 电化学诱导的环状酮的α-C—H胺化反应

Scheme 13. Electrochemically induced cyclic ketones α-C—H aminations

图式14. 电化学氧化诱导的[4+2]环化合成吡嗪

Scheme 14. Electrooxidation induced [4+2] annulation for the synthesis of pyrazines

图式15. 电化学引发的酮与2-氨基吡啶分子间环化反应

Scheme 15. Electrochemically initiated intermolecular cyclization of ketones with 2-aminopyridines

图式16. 电化学合成烯丙胺

Scheme 16. Electrochemical synthesis of allylamines

图式17. 电化学苄位C—H键胺化反应

Scheme 17. Electrochemical benzylic C—H amination reaction

图式18. 位点选择性的电化学苄基C—H键胺化反应

Scheme 18. Site-selective electrochemical benzylic C—H amination reaction

图式19. 锰催化的C(sp3)—H键的光电协同叠氮化反应

Scheme 19. Manganese-catalyzed electrophotochemical azidation of C(sp3)—H bonds

图式20. 电氧化诱导的分子内烯烃氢酰胺化反应

Scheme 20. Electrooxidation induced intramolecular olefin hydroamidation reaction

图式21. 多取代烯烃的电化学分子内氧化胺化反应

Scheme 21. Electrochemical oxidative intramolecular amination of multisubstituted alkenes

图式22. 脱氢[3+2]环化电化学合成(氮杂)吲哚啉类化合物

Scheme 22. Electrochemical synthesis of (aza)indolines via dehydrogenative [3+2] annulation

图式23. 电化学条件下自由基串联环化在7元碳环化合物合成中的应用

Scheme 23. Electrochemical synthesis of 7-membered carbocycles via tandem radical cyclization

图式24. 脒基自由基的电化学形成及其在C—H官能团化反应中的应用

Scheme 24. Amidinyl radical formation via anodic oxidation and its application in aromatic C—H bond functionalization

图式25. 阴极材料决定的二芳基酮肟电化学C—H官能团化反应

Scheme 25. Cathode material determined product selectivity for electrochemical C—H functionalization of biaryl ketoximes

图式26. C(sp2/sp3)—H键的区域选择性内酰胺化反应

Scheme 26. Regioselective intramolecular amidation of C(sp2/sp3)—H bonds

图式27. N-自由基引发的芳基远程迁移反应

Scheme 27. Nitrogen-centered radical induced aryl migration reaction

图式28. 电化学诱导的分子内C—H胺化

Scheme 28. Electrochemical induced intramolecular C—H amination

图式29. 二芳醛与NH3区域选择性合成N-杂芳烃

Scheme 29. Regioselective synthesis of N-heteroaromatics from biaryl aldehydes and NH3

图式30. 碘盐介导的电化学合成吲哚啉和吲哚

Scheme 30. Iodide-mediated electrosynthesis of indolines and indoles

图式31. 电化学合成3-叠氮基吲哚啉

Scheme 31. Electrochemical synthesis of 3-azido-indolines

图式32. 电化学条件下烯烃的氮杂环丙烷化反应

Scheme 32. Electrochemical aziridination of alkenes

图式33. 电氧化条件下喹喔啉酮的C—H胺化反应

Scheme 33. Electrooxidative C—H amination of quinoxalin- 2(1H)-ones

图式34. 电化学氧化诱导的分子间芳香族C—H酰亚胺化反应

Scheme 34. Electrooxidation induced intermolecular aromatic C—H imidation

图式35. 电化学氧化诱导的[3+2]环化反应制备吲哚啉类化合物

Scheme 35. Electrooxidation induced [3+2] annulation for the preparation of indolines

图式36. 电化学合成1,2,4-三唑杂环

Scheme 36. Electrochemical synthesis of 1,2,4-triazole-fused heterocycles

图式37. 酚类的电化学氧化C—H胺化反应

Scheme 37. Electrochemical oxidative C—H amination of phenols

图式38. 电化学氧化诱导的酪氨酸选择性修饰反应

Scheme 38. Electrochemical oxidation induced selective modification of biomolecules with tyrosine

图式39. 电化学合成噁嗪酮类化合物

Scheme 39. Electrochemical synthesis of oxazinones

图式40. 吲哚的电化学区域选择性磺酰化和肼化反应

Scheme 40. Electrochemically enabled chemoselective sulfonylation and hydrazination of indoles

图式41. 芳香醚的电化学邻位胺化反应

Scheme 41. Electrochemical ortho-selective amination of aromatic ethers

图式42. 电化学条件下通过C—C键断裂形成C—N键

Scheme 42. Electrochemical C—N bond formation through C—C bond cleavage

图式43. 三芳基乙烯的电化学氮杂环丙烷化反应

Scheme 43. Electrochemical aziridination of triaryl ethylenes

图式44. 基于烯烃活化实现烯烃的1,2-二胺基化反应

Scheme 44. 1,2-Diamination of alkenes via activation of alkenes

图式45. 电化学分子间C—H/N—H氧化交叉偶联反应

Scheme 45. Electrochemical intermolecular oxidative C—H/ N—H cross-coupling reaction

图式46. 电化学分子内C—H/N—H氧化交叉偶联反应

Scheme 46. Electrochemical intramolecular oxidative C—H/ N—H cross-couplings

图式47. 芳胺的对位选择性电化学胺化反应

Scheme 47. Electrochemical amination of aromatic amines with high para-selectivity

图式48. 金属催化烯烃的电化学双叠氮化反应

Scheme 48. Metal-catalyzed electrochemical alkene diazidation

图式49. 钴(II)催化的电化学氧化芳烃C—H胺化反应

Scheme 49. Cobalt(II)-catalyzed electrooxidative C—H amination of arenes

图式50. 镍催化的电氧化芳烃C—H胺化反应

Scheme 50. Nickel-catalyzed electrooxidative C—H amination of arenes

图式51. 钴催化的电化学C—H胺化反应

Scheme 51. Cobalt-catalyzed electrochemical C—H amination

图式52. 铜催化与电氧化协同作用的芳烃C(sp2)—H胺化反应

Scheme 52. Synergistic combination of copper catalysis and electrooxidation for C(sp2)—H amination

图式53. 铜催化的芳烃与仲胺的电化学C—H胺化反应

Scheme 53. Copper-catalyzed electrochemical C—H amination of arenes with secondary amines

图式54. 电化学合成高功能化(氮杂)吲哚

Scheme 54. Electrochemical synthesis of highly functionalized (aza)indoles

图式55. 电化学促进环化反应制备含氮多环芳烃

Scheme 55. Electrolytic cyclization leading to N-doped polycyclic aromatic hydrocarbons

图式56. 电化学合成咪唑稠合氮杂环化合物

Scheme 56. Electrochemical synthesis of imidazo-fused N- heteroaromatic compounds

图式57. 电化学合成苯并咪唑酮和苯并恶唑酮

Scheme 57. Electrosynthesis of benzimidazolones and benzoxazolones

图式58. 钴催化的电化学C—H/N—H活化

Scheme 58. Electrochemical C—H/N—H activation by cobalt catalysis

图式59. 钴催化的C—H活化实现联烯化合物的电化学氧化环化反应

Scheme 59. Cobalt-catalyzed electrooxidative C—H activation for the allene annulations

图式60. 钴催化内炔的电化学[4+2]环化反应

Scheme 60. Electrochemically cobalt-catalyzed [4+2] annulations of internal alkynes

图式61. 钴-电催化1,3-二炔的氧化C—H环化反应

Scheme 61. Cobalt-catalyzed electrooxidative C—H annulation with 1,3-diynes

图式62. 流动电化学化学技术协同金属铑催化的C—H环化反应

Scheme 62. Rh-catalyzed C—H annulation under electroflow conditions

图式63. 电化学协同金属铑催化的多米诺C—H环化反应合成氮杂多环芳烃

Scheme 63. Rh-catalyzed electrochemical synthesis of aza- nanographene

图式64. 钌催化的苯胺衍生物与炔烃的电化学脱氢环化反应

Scheme 64. Ruthenium-catalyzed electrochemical dehydrogenative annulation of anilines with alkynes

图式65. 酰胺和炔烃的电化学脱氢环化反应

Scheme 65. Electrochemically dehydrogenative annulation of amides with alkynes

图式66. 钴催化的电化学[4+2]环化反应

Scheme 66. Cobalt-catalyzed electrochemical [4+2] annulation reaction

图式67. 末端炔烃的电化学氧化氨基羰基化反应

Scheme 67. Electrochemical oxidative aminocarbonylation of terminal alkynes

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