Recent Progress of Visible Light-Induced the Synthesis of C(3) (Hetero)arylthio Indole Compounds

doi:10.6023/cjoc202308008

Abstract

The structure of 3-sulfenyl indoles widely exists in many drug molecules and natural product molecules. Its derivatives have extensive biological activities such as antibacterial, antiviral and anti-tumor, and are also important intermediates of organic synthesis and structural units of drug synthesis. Therefore, 3-sulfenyl indole compounds have great application value in the field of medicine. The research of its synthesis method has also become one of the current research hotspots. In this paper, the research progress in the synthesis of 3-sulfenyl indoles compounds in recent years is reviewed, and some reaction mechanisms are also discussed.

Key words: 3-sulfenyl indole, photocatalysis, C—S bond formation, synthesis

Cite this article

Qinggang Mei, Qinghan Li. Recent Progress of Visible Light-Induced the Synthesis of C(3) (Hetero)arylthio Indole Compounds[J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 398-408.

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Fig. & Tab. 27

Figure 1. 3-(Hetero)arylthio indole compounds with biological activity

Scheme 1. Synthesis route of 3-(hetero)arylthio indole compounds under visible light irradiation

Scheme 2. Visible light induced photoredox-catalyzed reaction of indoles with arylsulfonyl chlorides

Scheme 3. Possible reaction mechanism of the reaction of indoles with arylsulfonyl chlorides under visible light irradiation

Scheme 4. Preparation of 3-arylthio indole compounds by photocatalyzed reaction of indoles with thiophenols

Scheme 5. Possible reaction mechanism of the coupling reaction of indoles with thiophenols under visible light irradiation

Scheme 6. Preparation of 3-arylthioindole compounds by blue light induced reaction of indoles with thiophenols

Scheme 7. A plausible mechanism of the reaction of indoles with thiophenols under blue light irradiation

Scheme 8. Visible-light induced sulfenylation of indolizines with thiophenols

Scheme 9. Visible-light induced synthesis of 1,3-bissulfanyl indolizines

Scheme 10. Visible-light induced sulfenylation of indoles with thiophenols

Scheme 11. Possible reaction mechanism of the visible light induced sulfenylation of indoles with thiophenols

Scheme 12. Visible light induced sulfenylation of indoles C(3) in the presence of 60% (w) GO promoter

Scheme 13. Visible light induced sulfenylation of indoles C(3) in the presence of 50% (w) GO promoter

Scheme 14. The proposed mechanism for the sulfenylation of indoles C(3) in the presence of 50% (w) GO promoter

Scheme 15. B(C6F5)3-catalyzed aerobic oxidative C—S cross-coupling reaction of thiophenols with indoles under visible light irradiation

Scheme 16. Possible reaction mechanism of the coupling reaction of thiophenols with indoles under visible light irradiation

Scheme 17. Visible light-induced C(3) sulfenylation of indoles with diaryl disulfides

Scheme 18. Possible reaction mechanism of the C(3) sulfenylation of indoles with diaryl disulfides under visible light irradiation

Scheme 19. Photocatalyst-free, visible light-induced C(3) sulfenylation of indoles

Scheme 20. Possible reaction mechanism of the C(3) sulfenylation of indoles under visible light irradiation

Scheme 21. Visible light induced sulfenylation of indoles C(3) in the presence of I2.

Scheme 22. Proposed mechanism for the sulfenylation of indoles C(3) in the presence of I2 under blue light irradiation

Scheme 23. Visible-light-induced tandem oxidative cyclization of 2-alkynylanilines with disulfides

Scheme 24. Possible reaction mechanism of the tandem oxidative cyclization of 2-alkynylanilines with disulfides under visible light irradiation

Scheme 25. Visible light induced reaction of 2-alkynyl azide with thiophenols to prepare 3-arylthio indole compounds

Scheme 26. A plausible mechanism of the reaction of 2-alkynyl azides with thiophenols under visible light irradiation

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可见光促进C(3)(杂)芳硫基吲哚化合物的合成研究进展