电化学条件下喹喔啉-2(1H)-酮C(3)—H功能化的研究进展

doi:10.6023/cjoc202107042

有机化学 ›› 2021, Vol. 41 ›› Issue (12): 4610-4622.DOI: 10.6023/cjoc202107042 上一篇下一篇

所属专题：有机电合成虚拟专辑；绿色合成化学专辑

综述与进展

电化学条件下喹喔啉-2(1H)-酮C(3)—H功能化的研究进展

李丹丹^*(), 王晓辰, 李闪闪, 付晨雨, 李倩倩, 许东涛, 马莹莹

许昌学院化工与材料学院表面微纳米材料研究所河南省储能与转化微纳米材料重点实验室河南许昌 461000

收稿日期:2021-07-18 修回日期:2021-09-04 发布日期:2021-09-14
通讯作者: 李丹丹
基金资助:
国家自然科学基金(21901219); 河南教育厅重点项目(20B150024); 2021年度河南省高等教育青年骨干教师培养计划(2021GGJS146); 河南省药品质量控制与评价重点实验室(郑州大学)开放课题科研基金和许昌学院杰出青年骨干资助项目

Recent Advances in Electrochemical C(3)—H Functionalization of Quinoxalin-2(1H)-ones

Dandan Li(), Xiaochen Wang, Shanshan Li, Chenyu Fu, Qianqian Li, Dongtao Xu, Yingying Ma

Key Laboratory of Micro-Nano Materials for Energy Storage and Conversion of Henan Province, Institute of Surface Micro and Nano Materials, College of Chemical and Materials Engineering, Xuchang University, Xuchang, Henan 461000

Received:2021-07-18 Revised:2021-09-04 Published:2021-09-14
Contact: Dandan Li
Supported by:
National Natural Science Foundation of China(21901219); Key Project of Education Department of Henan Province(20B150024); Young Key Teacher Training Plan of Henan Provincial Higher Education in 2021(2021GGJS146); Open Subject Research Fund of the Key Laboratory of Drug Quality Control and Evaluation in Henan Province and the Young Backbone Teachers Project of Xuchang University

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摘要/Abstract

喹喔啉酮及其衍生物是一类重要的氮杂环化合物, 广泛存在于具有各种生物活性的天然产物、药物及功能材料中, 因此, 喹喔啉酮的C—H功能化引起了化学工作者的广泛关注. 电化学合成无需外加氧化还原试剂, 直接利用电子这一“清洁试剂”参与氧化还原反应, 具有反应条件温和及原子经济性好等特点, 十分符合绿色化学符合绿色化学和可持续发展的要求. 随着对电化学合成反应机理的深入研究以及反应设备的标准化, 该方法已经成为喹喔啉酮类化合物功能化的强有力工具. 综述了有机电化学在喹喔啉-2(1H)-酮C(3)—H功能化领域所取得的研究进展, 对反应的条件和机理进行了系统的总结, 并对该领域所面临的挑战及发展方向进行了展望与探讨.

关键词: 电化学, 喹喔啉-2(1H)-酮, C(3)—H功能化

Quinoxalinone and its derivatives are a class of important nitrogen heterocyclic compounds, which widely exist in natural products, drugs and functional materials. Therefore, the C—H functionalization of quinoxalinone has attracted extensive attention of chemical workers. In recent years, electrochemical synthesis directly uses electron as a “clean reagent” to participate in redox reaction without additional redox reagent, which has the characteristics of mild reaction conditions and good atom economy. This method meets the requirements of green chemistry and sustainable development. With the in-depth study on the mechanism of electrochemical synthesis and the standardization of reaction equipment, this method has become a powerful tool for functionalization of quinoxalineones. The recent advances in the electrochemical C(3)—H functionalization of quinoxaline-2(1H)-one are summarized. The reaction transformation conditions and mechanisms are systematically discussed, and the challenges and future directions of this field are included.

Key words: electrochemical synthesis, quinoxalin-2(1H)-one, C(3)—H functionalization

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李丹丹, 王晓辰, 李闪闪, 付晨雨, 李倩倩, 许东涛, 马莹莹. 电化学条件下喹喔啉-2(1H)-酮C(3)—H功能化的研究进展[J]. 有机化学, 2021, 41(12): 4610-4622.

Dandan Li, Xiaochen Wang, Shanshan Li, Chenyu Fu, Qianqian Li, Dongtao Xu, Yingying Ma. Recent Advances in Electrochemical C(3)—H Functionalization of Quinoxalin-2(1H)-ones[J]. Chinese Journal of Organic Chemistry, 2021, 41(12): 4610-4622.

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图/表 27

Scheme 1. Reaction pathways for electrochemical C(3)—H functionalization of quinoxalin-2-ones

Scheme 2. Nickel-catalyzed electrochemical reductive decarboxylative coupling of N-hydroxyphthalimide esters with quinoxalinones

Scheme 3. Possible mechanism

Scheme 4. Electrochemical decarboxylative C(3) alkylation of quinoxalin-2(1H)-ones

Scheme 5. Possible mechanism

Scheme 6. Electrochemical oxidative C—H alkylation of quinoxalin-2(1H)-ones with organoboron compounds

Scheme 7. Possible mechanism

Scheme 8. Electrochemical deoxygenative alkylation of quinoxalin-2(1H)-ones with alkyl carbazates

Scheme 9. Possible mechanism

Scheme 10. Electrochemical cross-coupling of C(sp2)—H with aryldiazonium salts via a paired electrolysis

Scheme 11. Possible mechanism

Scheme 12. Electrochemical heteroarylation of quinoxalin- 2(1H)-ones with pyrroles

Scheme 13. Electroreductive-induced C(3) pyridylation of quinoxalin-2(1H)-ones with cyanopyridines

Scheme 14. Possible mechanism

Scheme 15. Bromide ions-mediated electrosynthesis of Minisci- type trifluoromethylation of quinoxaline-2(1H)-ones

Scheme 16. Possible mechanism

Scheme 17. Electrooxidative C(3) cyanation of quinoxalin- 2(1H)-ones with TMSCN

Scheme 18. Possible mechanism

Scheme 19. Electro-oxidative C(3)—H amination of quinoxalin-2(1H)-ones

Scheme 20. Possible mechanism

Scheme 21. Electrochemical dehydrogenative C—H/O—H cross-coupling for the synthesis of 3-alkoxylated quinoxalin-2(1H)-ones

Scheme 22. Possible mechanism

Scheme 23. Electrooxidative cross-coupling for the synthesis of 3-thioquinoxalinones

Scheme 24. Possible mechanism

Scheme 25. Electrochemical phosphonation of quinoxalin-2(1H)-ones via C—H/P—H dehydrogenative cross-coupling

Scheme 26. Possible mechanism

Scheme 27. Electrochemical oxidative coupling of quinoxalin-2(1H)-ones with diarylphosphine oxides

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电化学条件下喹喔啉-2(1H)-酮C(3)—H功能化的研究进展

Recent Advances in Electrochemical C(3)—H Functionalization of Quinoxalin-2(1H)-ones

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