光促进过渡金属催化的C-杂原子键偶联反应进展

doi:10.6023/cjoc202202018

摘要/Abstract

光与过渡金属协同催化的偶联反应为金属催化偶联反应的发展提供了新的研究策略. 在这些催化体系中, 激发态光敏剂通过单电子转移过程调节过渡金属中间体的价态, 实现对偶联反应过程的调控, 尤其是传统过渡金属催化体系中难以发生的反应. 此外, 激发态光敏剂也可以通过能量转移过程促进过渡金属催化偶联反应的进行. 同时, 无外加光敏剂参与光促进过渡金属催化的C-杂原子键偶联反应也得到了快速发展. 光与过渡金属协同催化的偶联反应为构建C-杂原子键提供了重要方法, 展示了在合成化学中广阔的应用前景.

关键词: 光催化, 单电子转移, 能量转移, 过渡金属, 偶联反应

The photo-transition metal synergistically catalyzed coupling reaction provides a new research strategy for the development of metal-catalyzed coupling reactions. In this catalytic system, the excited state photosensitizer controls the valence state of the transition metal intermediate through a single electron transfer process, there by regulating the coupling reaction process, especially for the process that is difficult to occur in traditional transition metal catalysis. In addition, the excited photosensitizers could also promote the coupling reaction through the energy transfer process. Simultaneously, the light-promoted transition metal-catalyzed C—X bond coupling reactions without external photosensitizers have also been rapidly developed. Light and transition metals synergistically catalyzed coupling reactions provide an important tool for the construction of C-heteroatom bonds, showcasing broad application prospects in synthetic chemistry.

Key words: photocatalysis, single electron transfer, energy transfer, transition metal, coupling reaction

引用此文

宋戈洋, 薛东. 光促进过渡金属催化的C-杂原子键偶联反应进展[J]. 有机化学, 2022, 42(8): 2275-2299.

Geyang Song, Dong Xue. Research Progress on Light-Promoted Transition Metal-Catalyzed C-Heteroatom Bond Coupling Reactions[J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2275-2299.

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图/表 34

图式1. 可见光催化反应的主要方式

Scheme 1. Main mode of visible light catalyzed-reaction

图式2. 紫外光(UV)与Cu协同催化芳基C—N偶联反应

Scheme 2. Ultraviolet-promoted Cu-catalyzed aryl C—N coupling reactions

图式3. 紫外光与Cu协同催化芳基C—N偶联反应

Scheme 3. Ultraviolet-promoted Cu-catalyzed aryl C—N coupling reactions

图式4. 光镍协同催化芳基分子内C—N偶联反应

Scheme 4. Light-promoted Ni-catalyzed intramolecular aryl C—N coupling reactions

图式5. 光与Cu协同催化芳基C—N偶联反应

Scheme 5. Light-promoted Cu-catalyzed aryl C—N coupling reactions

图式6. 光镍协同催化芳基C—N偶联反应

Scheme 6. Light-promoted Ni-catalyzed aryl C—N coupling reactions

图式7. 光镍协同催化芳基C—N偶联反应

Scheme 7. Light-promoted Ni-catalyzed aryl C—N coupling reactions

图式8. 无外加光敏剂参与的光镍协同催化芳基C—N键偶联反应

Scheme 8. No photocatalyst participates in light-promoted Ni-catalyzed aryl C—N coupling reactions

图式9. 光镍协同催化无配体参与的芳基C—N偶联反应

Scheme 9. Light-promoted Ni-catalyzed ligand-free aryl C—N coupling reactions

图式10. 光镍协同催化芳基C—N偶联反应

Scheme 10. Light-promoted Ni-catalyzed aryl C—N coupling reactions

图式11. 无光敏剂参与光促进镍催化芳基C—N偶联反应

Scheme 11. No photocatalyst participates in light-promoted Ni- catalyzed aryl C—N coupling reactions

图式12. 非均相光镍协同催化芳基C—N键偶联反应

Scheme 12. Heterogeneous light-promoted Ni-catalyzed aryl C—N coupling reactions

图式13. 光与金属协同催化芳基C—N键偶联反应

Scheme 13. Light-promoted metal-catalyzed aryl C—N coupling reactions

图式14. 非均相光镍协同催化芳基C—N键偶联反应

Scheme 14. Heterogeneous light-promoted Ni-catalyzed aryl C—N coupling reactions

图式15. 无光敏剂参与的光镍催化手性芳基C—N键偶联反应

Scheme 15. No photocatalyst participates in light-promoted Ni-catalyzed chiral aryl C—N coupling reactions

图式16. 光镍协同催化芳基C—N键偶联反应

Scheme16. Light-promoted Ni-catalyzed aryl C—N coupling reactions

图式17. 光镍协同催化芳基C—N键偶联反应

Scheme17. Light-promoted Ni-catalyzed aryl C—N coupling reactions

图式18. 无光敏剂参与的光激发铁催化芳基硝化反应

Scheme 18. Light-excited iron-catalyzed nitration of aryl groups without photosensitizers

图式19. 光催化芳基C—S键偶联反应

Scheme 19. Light-promoted aryl C—S coupling reactions

图式20. 光铜协同催化芳基C—S键偶联反应

Scheme 20. Light-promoted Cu-catalyzed aryl C—S coupling reactions

图式21. 光镍协同催化芳基C—S键偶联反应

Scheme 21. Light-promoted Ni-catalyzed aryl C—S coupling reactions

图式22. 光镍协同催化芳基C—S键偶联反应

Scheme 22. Light-promoted Ni-catalyzed aryl C—S coupling reactions

图式23. 光镍协同催化芳基C—S键偶联反应

Scheme 23. Light-promoted Ni-catalyzed aryl C—S coupling reactions

图式24. 光镍协同催化芳基C—O键偶联反应

Scheme 24. Light-promoted Ni-catalyzed aryl C—O coupling reactions

图式25. 光铜协同催化芳基C—O键偶联反应

Scheme 25. Light-promoted Cu-catalyzed aryl C—O coupling reactions

图式26. 无光敏剂参与、光镍协同催化芳基C—O键偶联反应

Scheme 26. No photocatalyst participates in light-promoted Ni-catalyzed aryl C—O coupling reactions

图式27. 光镍协同催化手性芳基C—O键偶联反应

Scheme 27. Light-promoted Ni-catalyzed chiral aryl C—O coupling reactions

图式28. 光镍协同催化芳基C—O键偶联反应

Scheme 28. Light-promoted Ni-catalyzed aryl C—O coupling reactions

图式29. 光镍协同催化芳基C—O键偶联反应

Scheme 29. Light-promoted Ni-catalyzed aryl C—O coupling reactions

图式30. 非均相光镍协同催化芳基C—O键偶联反应

Scheme 30. Heterogeneous light-promoted Ni-catalyzed aryl C—O coupling reactions

图式31. 光镍协同催化芳基C—O键偶联反应

Scheme 31. Light-promoted Ni-catalyzed aryl C—O coupling reactions

图式32. 光铜协同催化芳基C—O键偶联反应

Scheme 32. Light-promoted Ni-catalyzed aryl C—O coupling reactions

图式33. 光镍协同催化芳基C—O键偶联反应

Scheme 33. Light-promoted Ni-catalyzed aryl C—O coupling reactions

图式34. 光镍协同催化芳基C—O键偶联反应

Scheme 34. Light-promoted Ni-catalyzed aryl C—O coupling reactions

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