Application on the Construction of Imidazo[1,2-a]pyridines C-3 Canbon-Hetero Bonds by Visible-Light Catalysis and Electrochemistry

doi:10.6023/cjoc202012026

Abstract

Imidazo[1,2-a]pyridines are a special nitrogen-containing compounds, which play an important role in the fields of pesticides biomedicine, optical and electrical materials. In recent years, the synthesis of functional imidazo[1,2-a]pyridines has become a hot topic for organic scientists and pharmaceutical chemists, and great progress has been made. Among them, the synthesis of functionalized imidazo[1,2-a]pyridines via visible-light catalysis and electrochemistry based on green chemistry has become the powerful tool for the synthesis of these compounds. Based on the types of canbon-hetero bonds of imidazo- [1,2-a]pyridines, the research on the construction of imidazo[1,2-a]pyridines C-3 canbon-hetero bonds by visible-light catalysis and electrochemical synthesis in recent 5 years is summarized.

Key words: imidazo[1,2-a]pyridine, visible-light catalysis, electrochemistry, carbon-hetero bond

Cite this article

Xiang Liu, Wen Li, Huanyu Liu, Hua Cao. Application on the Construction of Imidazo[1,2-a]pyridines C-3 Canbon-Hetero Bonds by Visible-Light Catalysis and Electrochemistry[J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 1759-1773.

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Fig. & Tab. 25

Figure 1. Representative drugs molecules containing imidazole[1,2-a]pyridines structure

Scheme 1. Aplication of synthesis of imidazolopyridine compounds via visible-light catalysis and electrochemistry

Figure 2. Common structures of photocatalysts

Scheme 2. Reaction mechanism of imidazo[1,2-a]pyridine catalyzed by visible-light

Scheme 3. Sulfonamidation of imidazo[1,2-a]pyridines catalyzed by visible-light

Scheme 4. Amination of imidazo[1,2-a]pyridines catalyzed by visible-light

Scheme 5. Regioselective cross dehydrogenative coupling of imidazo[1,2-a]pyridines catalyzed by visible-light

Scheme 6. Azo coupling of imidazo[1,2-a]pyridines catalyzed by visible-light

Scheme 7. C-3 alkoxylation of imidazo[1,2-a]pyridines with alcohols catalyzed by visible-light

Scheme 8. Thiocyanation of imidazo[1,2-a]pyridines catalyzed by visible-light

Scheme 9. Sulfenylation of imidazo[1,2-a]pyridines employing sulfinic acid catalyzed by visible-light

Scheme 10. Sulfenylation of imidazo[1,2-a]pyridines employing thiophenols catalyzed by visible-light

Scheme 11. C-3 sulfonylation of imidazo[1,2-a]pyridines catalyzed by visible-light

Scheme 12. Bromination of 2-arylimidazo[1,2-a]pyridines catalyzed by visible-light

Scheme 13. Selenylation of imidazo[1,2-a]pyridines

Scheme 14. Phosphorylation of imidazo[1,2-a]pyridines under photocatalysis

Scheme 15. Electrochemical oxidative C—H/N—H cross- coupling of imidazo[1,2-a]pyridines

Scheme 16. Electrochemical C—H/N—H oxidative cross- coupling of imidazo[1,2-a]pyridines with diarylamines

Scheme 17. Electrochemical oxidative C—H sulfenylation of imidazo[1,2-a]pyridines

Scheme 18. Electrochemical-induced regioselective C-3 thiomethylation of imidazo[1,2-a]pyridines

Scheme 19. Electrochemical oxidative C—H thiocyanation or selenocyanation of imidazo[1,2-a]pyridines

Scheme 20. Electrochemical oxidative selenylation of imidazo[1,2-a]pyridines

Scheme 21. Electrochemical oxidative C—H halogenation of imidazo[1,2-a]pyridines

Scheme 22. Electrochemical oxidative iodination of imidazo[1,2-a]pyridines

Scheme 23. Electrochemical oxidative phosphonylation of imidazo[1,2-a]pyridines

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可见光催化和电化学合成在咪唑并[1,2-a]吡啶3位碳-杂键构建中的应用