光/电催化喹喔啉酮官能团化反应研究进展

doi:10.1016/S1872-2067(21)63850-0

催化学报 ›› 2021, Vol. 42 ›› Issue (11): 1921-1943.DOI: 10.1016/S1872-2067(21)63850-0

光/电催化喹喔啉酮官能团化反应研究进展

孙凯^a,†, 肖芳^b,†, 於兵^a^,^*(), 何卫民^c^,^#()

^a郑州大学化学学院(绿色催化中心), 河南郑州450001
^b中南大学湘雅公共卫生学院, 湖南长沙410078
^c南华大学化学化工学院, 湖南衡阳421001

收稿日期:2021-03-29 修回日期:2021-03-29 接受日期:2021-05-13 出版日期:2021-11-18 发布日期:2021-08-22
通讯作者: 於兵,何卫民
作者简介:第一联系人：^†共同第一作者.
基金资助:
河南省自然科学基金(202300410375);国家自然科学基金(21971224);河南省博士后基金会(202003014);湖南省自然科学基金(2019JJ40090)

Photo-/electrocatalytic functionalization of quinoxalin-2(1H)-ones

Kai Sun^a,†, Fang Xiao^b,†, Bing Yu^a^,^*(), Wei-Min He^c^,^#()

^aGreen Catalysis Center, College of Chemistry, Zhengzhou University, Zhengzhou 450001, Henan, China
^bXiangya School of Public Health, Central South University, Changsha 410078, Hunan, China
^cSchool of Chemistry and Chemical Engineering, University of South China, Hengyang 421001, Hunan, China

Received:2021-03-29 Revised:2021-03-29 Accepted:2021-05-13 Online:2021-11-18 Published:2021-08-22
Contact: Bing Yu,Wei-Min He
About author:^#E-mail: weiminhe2016@yeah.net
^*E-mail: bingyu@zzu.edu.cn;
First author contact:^†Contributed equally to this work.
Supported by:
Natural Science Foundation of Henan Province(202300410375);National Natural Science Foundation of China(21971224);Henan Postdoctoral Foundation(202003014);Hunan Provincial Natural Science Foundation of China(2019JJ40090)

摘要/Abstract

摘要：

喹喔啉酮作为重要的含氮杂环骨架, 广泛应用于抗菌化合物、抗肿瘤药物、半导体材料中. 因此, 开发新方法合成不同官能团化喹喔啉酮以丰富其结构多样性在近年来广受关注. 在众多合成方法中, 喹喔啉酮的直接C-H官能团化是一类步骤经济性较高、简便高效地构建喹喔啉酮衍生物的重要方法. 近年来, 光催化、电催化和光电催化技术已发展成为现代有机合成中强有力的绿色合成工具, 可以有效利用光能或者电能促进有机化学转化, 减少传统有机反应中的高能耗. 过去几年, 化学工作者在光/电催化喹喔啉酮的直接C-H官能团化反应方面进行了大量研究, 开发了系列不同官能团化喹喔啉酮的绿色合成方法.
本文系统总结了喹喔啉酮的光/电催化官能团化研究最新进展, 重点讨论了光/电催化下自由基历程的喹喔啉酮C-H键直接官能团化反应, 反应类型主要包括喹喔啉酮的3-芳基化、3-烷基化、3-氟烷基化、3-烷氧基化、3-酰化、3-氨基化、3-膦酰化、3-巯基化、3-硅烷基化和环化反应等方面, 这将有助于理解光/电催化喹喔啉酮官能团化反应. 反应在温和条件下可以成功产生各种碳中心或杂原子为中心的自由基, 这些自由基进一步与喹喔啉酮的3-位进行加成反应, 进而开发出众多有效的方法来合成不同官能团化的喹喔啉酮. 这些条件温和的反应方法已经有部分成功应用于合成具有重要生物活性的喹喔啉酮化合物. 此外, 药物中常见的一些重要官能团, 例如三氟甲基和二氟甲基等可以顺利地引入到喹喔啉酮骨架结构, 这些研究为喹喔啉酮衍生物的生物活性相关研究奠定了基础.
本文还对当前光/电催化喹喔啉酮官能团化反应所面临的挑战和未来发展作了展望和总结, 期待在不久的将来, 有机合成工作者能基于喹喔啉酮的C-H键直接官能团化开发更多不同类型的新反应. 另一方面, 需要进一步开发新型的非均相可见光催化剂, 实现光催化剂的回收与再利用, 进一步降低反应成本, 促进其在药物开发、功能材料合成等应用方面的发展.

关键词: 光催化, 电催化, 喹喔啉酮, C-H官能团化

Abstract:

The photo-/electrocatalytic functionalization of quinoxalin-2(1H)-ones has emerged as a promising and powerful approach for post-synthetic modification of quinoxalin-2(1H)-ones. This review provides an overview of recent developments in photo-/electrocatalytic functionalization of quinoxalin-2(1H)-ones including arylation, alkylation, fluoroalkylation, amination, phosphorylation, acylation, alkoxylation, thiolation, silylation, and annulation. The reaction scope and the related mechanism are also well discussed.

Key words: Photocatalysis, Electrocatalysis, Quinoxalin-2(1H)-ones, C-H functionalization

孙凯, 肖芳, 於兵, 何卫民. 光/电催化喹喔啉酮官能团化反应研究进展[J]. 催化学报, 2021, 42(11): 1921-1943.

Kai Sun, Fang Xiao, Bing Yu, Wei-Min He. Photo-/electrocatalytic functionalization of quinoxalin-2(1H)-ones[J]. Chinese Journal of Catalysis, 2021, 42(11): 1921-1943.

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图/表 48

Scheme 1. TiO2-catalyzed synthesis of 3-arylated quinoxalin-2(1H)-ones.

Scheme 2. Eosin Y-catalyzed synthesis of 3-arylated quinoxalin-2(1H)-ones in DMF.

Scheme 3. 2D-COF-catalyzed synthesis of 3-arylated and 3-alkyl quinoxalin-2(1H)-ones.

Scheme 4. Photocatalyst-free strategy to access 3-arylated quinoxalin-2(1H)-ones.

Scheme 5. Photosynthesis of 3-arylated quinoxalin-2(1H)-ones with arylboronic acids.

Scheme 6. Electrosynthesis of 3-arylated quinoxalin-2(1H)-ones.

Scheme 7. Electrosynthesis for the pyridylation of quinoxalin-2(1H)-ones.

Scheme 8. Electro-oxidative C-H azolation of quinoxalin-2(1H)-ones.

Scheme 9. Ru(bpy)3Cl2-catalyzed synthesis of 3-alkyl quinoxalin-2(1H)-ones.

Scheme 10. Ir(ppy)3-catalyzed synthesis of 3-alkyl quinoxalin-2(1H)-ones.

Scheme 11. Ru(bpy)3Cl2-catalyzed decarboxylative reaction for the synthesis of 3-alkyl quinoxalin-2(1H)-ones.

Scheme 12. Eosin Y-catalyzed synthesis of 3-alkyl quinoxalin-2(1H)-ones.

Scheme 13. BI-OAc-accelerated synthesis of 3-alkyl quinoxalin-2(1H)-ones.

Scheme 14. Electrochemical decarboxylative protocol for 3-alkyl quinoxalin-2(1H)-ones.

Scheme 15. Electrochemical alkylation of quinoxalin-2(1H)-ones with alkyl boronic acids and their derivatives.

Scheme 16. Rose Bengal-catalyzed synthesis of 3-alkyl quinoxalin-2(1H)-ones.

Scheme 17. Eosin Y-catalyzed synthesis of 3-alkyl quinoxalin-2(1H)-ones with ethers.

Scheme 18. Eosin Y-catalyzed synthesis of 3-cyanoalkylated quinoxalin-2(1H)-ones.

Scheme 19. fac-Ir(ppy)3-catalyzed synthesis of 3-cyanoalkylated quinoxalin-2(1H)-ones.

Scheme 20. α-Perfluoroalkyl-β-heteroarylation of diverse alkenes.

Scheme 21. Three-component reaction of quinoxalin-2(1H)-ones, alkenes, and CF3SO2Na.

Scheme 22. Electrocatalytic trifluoromethylation of quinoxaline-2-ones.

Scheme 23. Photocatalytic trifluoromethylation of quinoxaline-2-ones.

Scheme 24. Photocatalytic perfluoroalkylation of quinoxaline-2-ones.

Scheme 25. Visible light and organoamine co-catalyzed difluoroalkylation of quinoxaline-2-ones.

Scheme 26. Visible-light-induced difluoroarylmethylation of quinoxaline-2-ones.

Scheme 27. Photocatalytic difluoromethylation of quinoxaline-2-ones.

Scheme 28. Eosin Y-catalyzed amination of quinoxalin-2(1H)-ones with aliphatic amines.

Scheme 29. Electrochemical amination of quinoxalin-2(1H)-ones with aliphatic amines.

Scheme 30. Rhodamine-B-catalyzed amidation of quinoxalin-2(1H)-ones.

Scheme 31. Photocatalyst-free method for the amination of quinoxalin-2(1H)-ones.

Scheme 32. Eosin Y-catalyzed phosphorylation of quinoxalin-2(1H)-ones.

Scheme 33. Photocatalyst-free method for the phosphorylation of quinoxalin-2(1H)-ones.

Scheme 34. Electrochemical phosphorylation of quinoxalin-2(1H)- ones.

Scheme 35. Electrochemical phosphorylated/pyrrole-functionalized quinoxalin-2(1H)-ones.

Scheme 36. Photocatalyst-free protocol for the synthesis of 3-acyl quinoxalin-2(1H)-ones.

Scheme 37. Strong-oxidant-free method for producing 3-acyl quinoxalin-2(1H)-ones.

Scheme 38. Eosin Y-catalyzed 3-acylation of quinoxalin-2(1H)-ones.

Scheme 39. Selective preparation of hydroxyl- and acyl-containing quinoxalin-2(1H)-ones.

Scheme 40. Photocatalytic alkoxylation of quinoxalin-2(1H)-ones.

Scheme 41. Electrochemical alkoxylation of quinoxalin-2(1H)-ones.

Scheme 42. Photocatalytic fluoroalkoxylation of quinoxalin-2(1H)-ones.

Scheme 43. Photocatalytic photocatalyst-free thiolation of quinoxalin-2(1H)-ones.

Scheme 44. Photocatalytic thiolation of quinoxalin-2(1H)-ones.

Scheme 45. Electrochemical thiolation of quinoxalin-2(1H)-ones.

Scheme 46. 3-Silylation of quinoxalinones.

Scheme 47. CsPbBr3-catalyzed annulation of quinoxalin-2(1H)-ones.

Scheme 48. g-C3N4-catalyzed annulation of quinoxalin-2(1H)-ones.

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光/电催化喹喔啉酮官能团化反应研究进展

Photo-/electrocatalytic functionalization of quinoxalin-2(1H)-ones

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