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

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

Abstract

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

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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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(21)63850-0

https://www.cjcatal.com/EN/Y2021/V42/I11/1921

Figures/Tables 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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