Recent Advances in Visible-Light-Induced C(3)—H Functionalization of Quinoxalinones under Transition-Metal-Free or Photocatalyst-Free

doi:10.6023/cjoc202307016

Abstract

Quinoxalinone and its derivatives are significant non-aromatic heterocycles existing in various bioactive natural products, pharmaceuticals, and functional materials, and exhibit an impressive spectrum of important biological properties. In recent years, the functionalization of quinoxalinones has attracted extensive attention of chemical workers, and important progress has made in the construction of C-3 substituted quinoxalinones by C—H functionalization. Photoredox catalysis has been widely used in the synthesis and conversions of organic compounds, because it can generate high reactive free radical intermediates under mild conditions using green and clean energy. Thus, photocatalysis synthesis is becoming powerful tools for C—H functionalization of quinoxalinone. This photocatalytic reactions under transition-metal-free or photocatalyst-free conditions meet the requirements of green chemistry and sustainable development, which have become a powerful tool for the functionalization of quinoxalinones and attracted the attention of many scholars. The research progress of C(3)—H functionalization of quinoxalinones by visible-light photoredox catalysis under transition-metal-free or photocatalyst-free conditions is reviewed during the past five years. The reaction mechanisms are systematically discussed, and the challenges and opportunities of this field are included.

Key words: quinoxalinone, photoredox, transition-metal-free, photocatalyst-free, C—H functionalization

Cite this article

Jianghu Dong, Liangming Xuan, Chi Wang, Chenxi Zhao, Haifeng Wang, Qiongjiao Yan, Wei Wang, Fen'er Chen. Recent Advances in Visible-Light-Induced C(3)—H Functionalization of Quinoxalinones under Transition-Metal-Free or Photocatalyst-Free[J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 111-136.

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Fig. & Tab. 45

Figure 1. Selected bioactive C(3)-substituted quinazolinones

Figure 2. Structures of common organic photocatalysts

Scheme 1. Two reaction pathways of C(3) functionalization of quinazolinones under visible-light-induced transition-metal-free conditions

Scheme 2. Visible-light-promoted direct C—H/C—H cross-coupling reaction of quinazolinones with ethers

Scheme 3. Visible-light-promoted cross-coupling reaction of quinazolinones with ethers

Scheme 4. Photocatalytic cyanoalkylation of quinazolinones with cyclobutanone oxime esters

Scheme 5. Visible-light-promoted decarboxylative heteroarylation of amino acids

Scheme 6. Visible-light-induced direct alkylation of heteroaromatics

Scheme 7. Photocatalytic intramolecular cyclization/alkylation of quinazolinones with bromodifluoroacetamides

Scheme 8. Transition metal-free photocatalytic benzylation of quinazolinones

Scheme 9. Visible-light induced C—H benzylation of quinazolinones

Scheme 10. Photocatalytic C-3 alkylation of Katritzky salt and quinazolinones

Scheme 11. Transition-metal-free visible-light-induced acetalization of quinazolinones

Scheme 12. Visible-light-driven arylation of quinazolinones

Scheme 13. Visible-light-induced oxidative coupling reaction of quinazolinones with pyrrole derivatives

Scheme 14. Photocatalytic decarboxylative acylation of α-oxocarboxylic acids with quinazolinones

Scheme 15. Visible-light photocatalytic C—H acylation of quinazolinones with aldehydes

Scheme 16. Visible-light-promoted C—N cross-coupling reaction of quinazolinones with amines

Scheme 17. Photocatalytic arylamination of quinazolinones with benzotriazoles

Scheme 18. Visible-light-driven C—H/O—H dehydrogenative coupling reaction of quinazolinones with alcohols

Scheme 19. Visible-light-promoted sulfur dioxide insertion reaction of multi components

Scheme 20. Photoinduced three-component tandem reaction of quinazolinones, olefins with sodium trifluoromethylsulfinates or sulfinic acids

Scheme 21. Photocatalytic three-component coupling reaction of quinazolinones

Scheme 22. Visible light photoredox-catalyzed phosphorylation of quinazolinones

Scheme 23. Visible-light-promoted C—S cross-coupling reaction of quinazolinones with thiols

Scheme 24. Photoredox-catalyzed C—H silylation of quinoxalinones or electron-deficient heteroarenes

Scheme 25. Visible-light-driven C(3) alkylation and arylation of quinazolinones

Scheme 26. Photocatalytic trifluoroalkylation and trifluoroalkenylation of quinazolinones

Scheme 27. Visible-light-driven thiolation of quinazolinones

Scheme 28. OCN promoted the arylation reaction of quinoxalinone with aryl diazonium salts

Scheme 29. Photocatalytic arylation of quinazolinones with arylhydrazines

Scheme 30. Visible-light-promoted cross-dehydrogenative coupling reaction of quinoxalinone with thiols

Scheme 31. Photocatalytic C(3)—H alkylation of quinazolinones

Scheme 32. Photocatalytic direct C—H arylation of quinazolinones with aroyl peroxides

Scheme 33. Photocatalytic amidation of quinazolinones

Scheme 34. Visible-light-promoted three-component difluoroalkylation of quinoxalinones, olefins and difluoroiodine reagents

Scheme 35. Photocatalytic the arylation reaction of N-heterocyclic compounds

Scheme 36. Photocatalytic hydrochloric acid-mediated C(3)—H arylation of quinoxalines with arylhydrazines

Scheme 37. Visible light promoted thioalkylation of quinoxalinones with olefins and aryl disulfides

Scheme 38. Photocatalytic remote C(sp3)—H heteroarylation of N-fluorocarboxamides with quinazolinones

Scheme 39. Photocatalytic alkylation and oxidation of quinazolinones under photocatalyst-free conditions

Scheme 40. Photocatalytic decarbonylative C—H alkylation of quinazolinones with aliphatic aldehydes

Scheme 41. Visible-light-driven direct decarboxylative coupling reaction of NHPI esters with quinazolinones

Scheme 42. Photocatalytic alkylation between quinazolinones and Katritzky salts

Scheme 43. Visible-light-promoted tandem radical cyclization/heteroarylation of N-allylbromodifluoroacetamides with quinazolinones

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