Research Progress on Light-Promoted Transition Metal-Catalyzed C-Heteroatom Bond Coupling Reactions

doi:10.6023/cjoc202202018

Abstract

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

Cite this article

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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Fig. & Tab. 34

Scheme 1. Main mode of visible light catalyzed-reaction

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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