捕捉环加成反应中的有机亚铜中间体构筑氮杂环化合物研究进展

doi:10.6023/A22100419

摘要/Abstract

铜(I)盐催化的环加成反应, 如叠氮-炔[3+2]环加成(CuAAC)、不饱和化合物与异氰基化合物的[3+2]环加成、硝酮-炔的环加成(Kinugasa反应)是构建多类氮杂环的高效合成方法, 被广泛应用于有机合成的各个领域. 近年来, 针对几类环加成反应中产生的有机亚铜中间体的多样性转化吸引了国内外很多课题组的注意, 基于对这些环加成反应中有机亚铜中间体的捕捉, 多类串联及多组分反应得以发展, 从而成功实现了一系列多取代杂环或稠环结构的高效构建. 本综述总结了这一领域的研究进展, 按照所经历的有机亚铜中间体的类型进行分类, 包括: (1) CuAAC反应中产生的三氮唑亚铜中间体; (2) 炔烃与异氰化合物[3+2]环加成反应中产生的2H-吡咯基亚铜中间体; (3) Kinugasa反应中产生的烯醇亚铜中间体. 期望此综述能够有助于研究者了解有机亚铜中间体捕捉策略的发展、应用现状及不足之处, 进一步推动铜催化转化的发展.

关键词: 铜催化, 有机亚铜中间体, 氮杂环化合物, 串联反应, 一锅反应

Copper(I)-catalyzed cycloaddition reactions, such as [3+2] cycloaddition of organic azides with terminal alkynes (CuAAC), unsaturated compounds with isocyanides, and nitrones with alkynes (Kinugasa reaction), are important methods for the constructions of different types of nitrogen-containing heterocycles. Great progresses have been achieved in such transformations and widely applied in various fields of organic syntheses. In these cycloaddition reactions, similar organocopper(I) intermediates are generated in situ, and can be trapped with additional electrophiles for further tandem or one-pot transformations. The development of the strategy to trap organocopper(I) intermediates in these reactions provides practical and efficient methods for the construction of multisubstituted or fused nitrogen-containing heterocycles. The advances in this area are summarized in this review: (1) trapping organocopper(I) intermediates in CuAAC reaction; (2) trapping organocopper(I) intermediates in the [3+2] cycloaddition of isocyanides with electron-deficient alkynes; (3) trapping enolate organocopper(I) intermediates in Kinugasa reaction. The review may be helpful for researchers to better understand the development and limitations for the trapping of organocopper(I) intermediates.

Key words: copper catalysis, organocopper(I) intermediate, nitrogen-containing heterocycles, tandem reaction, one-pot reaction

引用此文

邱孔茜, 李杰, 马浩文, 周伟, 蔡倩. 捕捉环加成反应中的有机亚铜中间体构筑氮杂环化合物研究进展[J]. 化学学报, 2023, 81(1): 42-63.

Kongxi Qiu, Jie Li, Haowen Ma, Wei Zhou, Qian Cai. Recent Advances in the Construction of Nitrogen-Containing Heterocycles via Trapping Organocopper(I) Intermediates[J]. Acta Chimica Sinica, 2023, 81(1): 42-63.

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图/表 57

图1. 捕捉环加成反应中的有机亚铜中间体构建氮杂环化合物

Figure 1. The construction of nitrogen-containing heterocycles via trapping organocopper(I) intermediates in cycloaddition reactions

图2. CuAAC反应机理

Figure 2. Proposed mechanism for CuAAC reaction

图3. 高活性亲电试剂捕捉CuAAC反应中间体

Figure 3. Trapping the CuAAC intermediates with highly electrophilic reagents

图4. 烯丙基碘捕捉CuAAC反应中间体

Figure 4. Trapping the CuAAC intermediate with allyl iodine

图5. 捕捉CuAAC反应联合关环复分解构建双环三氮唑

Figure 5. Synthesis of bicyclic triazoles via interrupted CuAAC reaction and ring-closing metathesis

图6. 原位生成的碘正离子捕捉CuAAC反应中间体

Figure 6. Trapping the CuAAC intermediates with in situ generated I+

图7. NBS捕捉CuAAC反应中间体

Figure 7. Trapping the CuAAC intermediates with NBS

图8. 捕捉CuAAC反应中间体合成三氮唑核苷类化合物

Figure 8. Synthesis of triazolyl-nucleosides via trapping the CuAAC intermediates

图9. 捕捉有机叠氮-炔铜反应的CuAAC反应中间体

Figure 9. Trapping the CuAAC intermediates from azides and 1-copper(I) alkynes

图10. 125I捕捉CuAAC反应中间体

Figure 10. Trapping the CuAAC intermediates with an 125I electrophile

图11. 铜催化[3+2]/C—N偶联构建三氮唑并喹喔啉

Figure 11. Synthesis of [1,2,3]triazolo[1,5-a]quinoxalines via Cu(I)-catalyzed [3+2] cycloaddition/Ullmann C—N coupling

图12. 铜催化[3+2]/C—N偶联构建三氮唑并喹喔啉酮

Figure 12. Synthesis of triazolo-[1,5-a]quinoxalin-4(5H)-ones via Cu(I)-catalyzed [3+2] cycloaddition/Ullmann C—N coupling process

图13. [3+2]环加成/C—N偶联构建三氮唑并苯并二氮杂卓酮类化合物

Figure 13. Tandem [3+2] cycloaddition/C—N coupling process for triazolo [1,5-a][1,4]benzodiazepinones

图14. Ugi四组分反应联合铜(I)催化反应构建三氮唑并苯并二氮杂卓酮类化合物

Figure 14. Synthesis of triazolo[1,5-a][1,4]benzodiazepinones via Ugi 4-CR and copper-catalyzed reactions

图15. CuI催化[3+2]/C—N偶联构建三氮唑稠合环磺酰胺

Figure 15. Synthesis of triazolo-1,2,4-benzothiadiazine-1,1-dioxides via Cu(I)-catalyzed [3+2] cycloaddition/C—N coupling process

图16. Ugi四组分反应联合铜(I)催化反应构建三氮唑并喹喔啉酮类化合物

Figure 16. Synthesis of triazolo[1,5-a]quinoxalines via Ugi 4-CR and copper(I)-catalyzed reaction

图17. 铜(I)催化[3+2]环加成/烯基C—N偶联串联环化

Figure 17. Cu(I)-catalyzed [3+2] cycloaddition/alkenyl C—N coupl- ing tandem reaction

图18. CuAAC/Ullmann C—C偶联反应

Figure 18. Copper(I)-catalyzed CuAAC/Ullmann C—C coupling

图19. CuAAC/C—N偶联构建FTQuon

Figure 19. Synthesis of FTQuon via CuAAC/C—N coupling process

图20. CuAAC/分子内C—C偶联构建三氮唑稠合环醚

Figure 20. Synthesis of fused triazoles via tandem CuAAC/intram- olecular C—C coupling

图21. CuAAC/芳基化偶联反应

Figure 21. CuAAC/direct arylation

图22. CuAAC/C—N偶联/分子内芳基化反应

Figure 22. Tandem CuAAC/C—N coupling/intramolecular arylation

图23. 环状二芳基碘鎓盐、叠氮化钠与炔烃的三组分串联反应

Figure 23. Cascade reaction of cyclic diaryliodoniums, sodium azide, and alkynes

图24. CuAAC/分子内酰基化反应

Figure 24. CuAAC/Intramolecular acylation

图25. 叠氮化合物、炔烃及芳基卤代物三组分Cu/Pd接力转金属化反应

Figure 25. Three-component click reaction of azide, alkyne and aryl halide via Cu/Pd transmetalation relay catalysis

图26. 铜(I)催化叠氮化物、炔烃及磺腙三组分串联反应

Figure 26. Cu(I)-catalyzed three-component reactions of azides, alkynes and N-tosylhydrazones

图27. 铜(I)催化叠氮化合物、炔烃及重氮化合物三组分串联反应

Figure 27. Cu(I)-catalyzed three-component reaction of azides, alkynes and diazo compounds

图28. 炔基溴化合物捕捉CuAAC反应中间体

Figure 28. Trapping the CuAAC intermediates with bromoalkynes

图29. 2H-氮杂丙烯啶与炔丙醇碳酸酯捕捉CuAAC反应中间体

Figure 29. Trapping CuAAC intermediates with 2H-azirine and propargylic carbonates

图30. TMSCF3捕捉CuAAC反应中间体

Figure 30. Trapping the CuAAC intermediates with TMSCF3

图31. TFAA促进的CuAAC反应

Figure 31. TFAA promoted CuAAC reaction

图32. N/S亲电试剂捕捉CuAAC反应中间体

Figure 32. Trapping the CuAAC intermediates with N/S electrophiles

图33. CuAAC串联分子内C—S偶联反应

Figure 33. Tandem CuAAC/intramolecular C—S coupling reaction

图34. CuAAC反应串联分子内C—S偶联反应

Figure 34. Tandem CuAAC/intramolecular C—S coupling reaction

图35. CuAAC反应串联C—Sn偶联反应

Figure 35. Tandem CuAAC/C—Sn coupling reaction

图36. CuAAC反应串联C—C氧化偶联

Figure 36. Tandem CuAAC/C—C oxidative coupling

图37. CuAAC/C—C氧化偶联合成5-炔基取代三氮唑

Figure 37. Synthesis of 5-alkynyl 1,2,3-triazoles via CuAAC/C—C oxidative coupling

图38. CuAAC反应串联C—P氧化偶联

Figure 38. Tandem CuAAC/C—P oxidative coupling reaction

图39. 三氮唑亚铜中间体的可控转化

Figure 39. Controllable transformations of triazolyl-copper(I) intermediate

图40. CuAAC反应联合分子内C—H酰胺化

Figure 40. Tandem CuAAC and intramolecular C—H amidation

图41. CuAAC反应串联分子内C—N氧化偶联

Figure 41. Tandem CuAAC/intramolecular C—N oxidative coupling reaction

图42. CuAAC反应串联分子间C—N氧化偶联

Figure 42. Tandem CuAAC/intermolecular C—N oxidative coupling reaction

图43. 以芳基硼酸捕捉CuAAC反应

Figure 43. Trapping the CuAAC intermediates with arylboronic acids

图44. 铜催化炔丙酸、叠氮和芳基硼酸三组分脱羧/环加成/偶联

Figure 44. Copper-catalyzed decarboxylative cycloaddition/coupling of propiolic acids, azides and arylboronic acids

图45. 螯合辅助的CuAAC反应串联分子间C—N氧化偶联

Figure 45. Chelation-assisted tandem CuAAC/intermolecular C—N oxidative coupling reaction

图46. 铜(I)催化异氰基乙酸酯类化合物与炔烃[3+2]环加成反应

Figure 46. Copper(I)-catalyzed [3+2] cycloaddition of isocyanides with acetylene

图47. 铜(I)催化异氰化合物与邻碘代炔酮化合物串联环化

Figure 47. Copper-catalyzed tandem reactions of isocyanides with 1-(2-iodoary)-2-yn-1-ones

图48. 铜(I)催化异氰化合物与邻卤代烯酮类化合物串联环化

Figure 48. Copper(I)-catalyzed tandem reactions of isocyanides with 1-(2-haloaryl)enones

图49. 铜(I)催化异氰化合物与N-(2-卤代芳基)丙炔酰胺类化合物串联环化

Figure 49. Copper(I)-catalyzed tandem reaction of isocyanides with N-(2-haloaryl)propiolamides

图50. 铜(I)催化异氰化合物与N-(2-碘代芳基)炔亚胺类化合物串联环化

Figure 50. Copper(I)-catalyzed tandem reactions of isocyanides with N-(σ-iodoaryl)alkynylimines

图51. 铜(I)催化异氰化合物与炔酮衍生物串联环化构建吡咯稠合四环骨架分子

Figure 51. Copper(I)-catalyzed tandem annulation of 2-alkynoyl-2'- iodo-1,1'-biphenyls with isocyanoacetates for the construction of pyrrole- fused tetracyclic skeletons

图52. Kinugasa反应机理

Figure 52. Proposed mechanism for Kinugasa reaction

图53. 烯丙基碘捕捉Kinugasa反应中间体

Figure 53. Trapping the Kinugasa intermediates with allyl iodide

图54. 以分子内迈克尔加成反应捕捉Kinugasa反应中间体

Figure 54. Trapping the Kinugasa intermediates for intramolecular Michael addition reaction

图55. 亲电硫试剂捕捉Kinugasa反应中间体

Figure 55. Trapping the Kinugasa intermediates with S-electrophiles

图56. 钯/铜协同催化多组分Kinugasa反应

Figure 56. Synergistic copper/palladium-catalyzed multicomponent Kinugasa reaction

图57. Kinugasa/分子内C—C偶联串联反应

Figure 57. Tandem Kinugasa/intramolecular C—C coupling

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