Recent Advances in the Construction of Nitrogen-Containing Heterocycles via Trapping Organocopper(I) Intermediates

doi:10.6023/A22100419

Abstract

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

Cite this article

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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Fig. & Tab. 57

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

Figure 2. Proposed mechanism for CuAAC reaction

Figure 3. Trapping the CuAAC intermediates with highly electrophilic reagents

Figure 4. Trapping the CuAAC intermediate with allyl iodine

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

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

Figure 7. Trapping the CuAAC intermediates with NBS

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

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

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

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

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

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

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

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

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

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

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

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

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

Figure 21. CuAAC/direct arylation

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

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

Figure 24. CuAAC/Intramolecular acylation

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

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

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

Figure 28. Trapping the CuAAC intermediates with bromoalkynes

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

Figure 30. Trapping the CuAAC intermediates with TMSCF3

Figure 31. TFAA promoted CuAAC reaction

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

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

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

Figure 35. Tandem CuAAC/C—Sn coupling reaction

Figure 36. Tandem CuAAC/C—C oxidative coupling

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

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

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

Figure 40. Tandem CuAAC and intramolecular C—H amidation

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

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

Figure 43. Trapping the CuAAC intermediates with arylboronic acids

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

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

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

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

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

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

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

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

Figure 52. Proposed mechanism for Kinugasa reaction

Figure 53. Trapping the Kinugasa intermediates with allyl iodide

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

Figure 55. Trapping the Kinugasa intermediates with S-electrophiles

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

Figure 57. Tandem Kinugasa/intramolecular C—C coupling

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