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

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (5): 1759-1773.DOI: 10.6023/cjoc202012026 Previous Articles Next Articles

Special Issue: 有机电合成虚拟专辑；有机光催化虚拟合辑

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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

刘想¹^,^*(), 李文¹, 刘环宇¹, 曹华¹^,^*()

1 广东药科大学医药化工学院广东省化妆品工程技术研究中心广东中山 528458

收稿日期:2020-12-16 修回日期:2021-01-11 发布日期:2021-02-07
通讯作者: 刘想, 曹华
基金资助:
国家自然科学基金(22001045); 广东省广东药科大学创新强校项目(2019KQNCX061); 广东省中山市共建重点学科建设专项资金资助项目

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

Xiang Liu¹^,^*(), Wen Li¹, Huanyu Liu¹, Hua Cao¹^,^*()

1 Guangdong Cosmetics Engineering & Technology Research Center, School of Chemistry and Chemical Engineering, Guangdong Pharmaceutical University, Zhongshan, Guangdong 528458

Received:2020-12-16 Revised:2021-01-11 Published:2021-02-07
Contact: Xiang Liu, Hua Cao
About author:
* Corresponding authors. E-mail: liux96@gdpu.edu.cn;
E-mail: caohua1@gdpu.edu.cn
Supported by:
National Natural Science Foundation of China(22001045); Innovation and Strong School Project of Guangdong Pharmaceutical University(2019KQNCX061); Special Funds of Key Disciplines Construction from Guangdong and Zhongshan Cooperating

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

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

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