Recent Advances in Photo-Induced Oxindole Formation from N-Arylacrylamides

doi:10.6023/cjoc202407017

Abstract

Oxindole scaffold is a highly valuable structural motif and its synthesis research is of great significance. N-Aryl-acrylamides have been the important raw materials for the synthesis of oxindoles, because of their high reactivity, cheap and ready availability. In recent years, photo-mediated N-arylacrylamides engaged in radical cyclization reactions have made a great advance, which has received considerable attention. The research progress is systematically summarized, including radical coupling and cyclization reactions of N-arylacrylamides with alkyl, fluorinated alkyl, acyl, sulfonyl radical precursors, and among others. Advantages and disadvantages, substrate scope, and mechanisms of these methods were discussed.

Key words: oxindole, N-arylacrylamide, radical reaction, photocatalysis

Cite this article

Yongbo Tan, Hongbo Shu, Huawen Huang. Recent Advances in Photo-Induced Oxindole Formation from N-Arylacrylamides[J]. Chinese Journal of Organic Chemistry, 2025, 45(6): 2086-2108.

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Fig. & Tab. 47

Figure 1. Bioactive molecules and natural products with 2-oxin-dole as the core

Scheme 1. Decarboxylation/C—H functionalization reactions by photoredox catalysis

Scheme 2. Radical tandem reaction involving N-hydroxy-phthalimide ester

Scheme 3. Radical tandem reactions involving bromomethyl aryl sulfone

Scheme 4. Methylarylation of N-arylacrylamides

Scheme 5. Radical tandem reactions involving bromoacetonitrile

Scheme 6. Radical tandem reactions involving acetonitrile

Scheme 7. Radical tandem reactions involving simple ethers

Scheme 8. Deboronative alkylarylation of N-arylacrylamides with organoboronic acids

Scheme 9. EDA complex mediated reactions of N-arylacrylamides with Katritzky salts

Scheme 10. Visible-light-mediated reactions of aldehydes with N-arylacrylamides

Scheme 11. Photoinduced palladium-catalyzed synthesis of alkyl oxindoles

Scheme 12. Visible-light-mediated reactions of hydroxyketones with N-arylacrylamides

Scheme 13. Photoredox-mediated carbon radical formation from sulfoxonium ylides

Scheme 14. Visible-light-mediated acylarylation of N-arylacrylamides

Scheme 15. Anhydride participating in construction of acyl oxindoles

Scheme 16. Radical tandem reactions involving α-oxocarboxylic acids

Scheme 17. Visible-light-mediated reactions of aroyl chlorides with N-arylacrylamides

Scheme 18. Photoredox-mediated acyl radical formation from oxime ester

Scheme 19. CTC-Mediated synthesis of oxindole scaffolds

Scheme 20. Excited-state copper catalyzed synthesis of aroyl oxindole

Scheme 21. Catalyst-and additive-free construction of acyl oxindole scaffolds

Scheme 22. Visible-light-mediated synthesis of trifluoromethyl oxindoles

Scheme 23. Visible-light-mediated synthesis of fluorinated oxindoles

Scheme 24. Radical tandem reactions involving sodium trifluoromethanesulfinate

Scheme 25. Catalyst-and additive-free synthesis of trifluoromethyl oxindoles

Scheme 26. Trifluoromethylarylation of N-arylacrylamides involving triflic anhydride

Scheme 27. Trifluoromethylarylation of N-arylacrylamides involving TFAA

Scheme 28. Photohomolysis of CF3SO2Cl for N-arylacrylamides trifluoromethylarylation

Scheme 29. Radical tandem reaction involving ehyl bromodifluoroacetate

Scheme 30. Visible-light-mediated synthesis of difluoromethyl oxindoles

Scheme 31. Difluoroacetic acid for the synthesis of difluoromethyl oxindoles

Scheme 32. Selective single C(sp3)—F bond activation of trifluoromethylarenes

Scheme 33. Selective single C(sp3)—F bond activation of trifluoromethyl ketones

Scheme 34. Selective single C(sp3)—F bond activation of ethyl trifluoroacetate

Scheme 35. Visible-light-mediated synthesis of sulfonated oxindoles

Scheme 36. Visible-light-induced three components reactions

Scheme 37. Visible-light-mediated selective synthesis of sulfonates and sulfonamides

Scheme 38. Visible-light-induced synthesis of monofluoromethylsufonyl oxindoles

Scheme 39. Radical tandem reactions involving aryl diazonium salts

Scheme 40. Synthesis of 3,3-disubstituted oxindoles involving (hetero)aryl halides

Scheme 41. Trichloromethylarylation of N-arylacrylamides

Scheme 42. Synthesis of hydroxyalkyl oxindoles

Scheme 43. Catalyst-and additive-free synthesis of trifluoromethyl oxindoles

Scheme 44. PCET enabled hydroarylation of N-arylacrylamides

Scheme 45. Intramolecular hydroarylation of alkenes using cobalt-photoredox dual catalysis

Scheme 46. CTC mediated hydroarylation of N-arylacrylamides

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