光诱导N-芳基丙烯酰胺参与的吲哚酮合成研究进展

doi:10.6023/cjoc202407017

摘要/Abstract

吲哚酮骨架是一种非常有价值的结构单元, 其合成研究具有重要意义. N-芳基丙烯酰胺类化合物反应活性好, 廉价易得, 是合成吲哚酮衍生物的重要原料. 近年来光介导N-芳基丙烯酰胺参与的自由基环化反应取得了重要的研究进展, 引起了广泛关注. 系统综述了这一领域的最新研究进展, 主要包括N-芳基丙烯酰胺与烷基自由基前体、含氟烷基自由基前体、酰基自由基前体、磺酰基自由基前体及其它类型自由基前体的自由基偶联环化反应等, 讨论了这些光催化体系的优缺点、底物范围及反应机理等.

关键词: 吲哚酮, N-芳基丙烯酰胺, 自由基反应, 光催化

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

引用此文

谭永波, 舒洪波, 黄华文. 光诱导N-芳基丙烯酰胺参与的吲哚酮合成研究进展[J]. 有机化学, 2025, 45(6): 2086-2108.

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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图/表 47

图1. 2-吲哚酮为核心的生物活性分子和天然产物

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

图式1. 光氧化还原催化的脱酸/碳氢键官能团化反应

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

图式2. N-羟基邻苯二甲酰亚胺酯参与的自由基串联反应

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

图式3. 溴甲基芳基砜参与的自由基串联反应

Scheme 3. Radical tandem reactions involving bromomethyl aryl sulfone

图式4. N-芳基丙烯酰胺的甲基芳化

Scheme 4. Methylarylation of N-arylacrylamides

图式5. 溴代乙腈参与的自由基串联反应

Scheme 5. Radical tandem reactions involving bromoacetonitrile

图式6. 乙腈参与的自由基串联反应

Scheme 6. Radical tandem reactions involving acetonitrile

图式7. 简单醚参与的自由基串联反应

Scheme 7. Radical tandem reactions involving simple ethers

图式8. N-芳基丙烯酰胺与有机硼酸的脱硼烷芳化

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

图式9. 电子供体受体复合物介导的N-芳基丙烯酰胺与katritzky盐的反应

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

图式10. 可见光介导的醛与N-芳基丙烯酰胺的反应

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

图式11. 光诱导的钯催化的烷基吲哚酮衍生物的合成

Scheme 11. Photoinduced palladium-catalyzed synthesis of alkyl oxindoles

图式12. 可见光介导的羟基苯乙酮与N-芳基丙烯酰胺的反应

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

图式13. 光氧化还原介导的硫氧叶立德生成碳自由基

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

图式14. 可见光介导的N-芳基丙烯酰胺的酰芳化

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

图式15. 酸酐参与酰化吲哚酮衍生物的构建

Scheme 15. Anhydride participating in construction of acyl oxindoles

图式16. α-氧代羧酸参与的自由基串联反应

Scheme 16. Radical tandem reactions involving α-oxocarboxylic acids

图式17. 可见光介导的芳基酰氯与N-芳基丙烯酰胺的反应

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

图式18. 光氧化还原介导的肟酯产生酰基自由基

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

图式19. 电荷转移复合物介导的吲哚酮骨架的合成

Scheme 19. CTC-Mediated synthesis of oxindole scaffolds

图式20. 激发态铜催化的芳酰基化的吲哚酮骨架的合成

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

图式21. 无催化剂和添加剂的吲哚酮骨架构建

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

图式22. 可见光介导的三氟甲基化吲哚酮衍生物的合成

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

图式23. 可见光介导的氟化吲哚酮衍生物的合成

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

图式24. 三氟甲基亚磺酸钠参与的自由基串联反应

Scheme 24. Radical tandem reactions involving sodium trifluoromethanesulfinate

图式25. 无催化剂和添加剂的三氟甲基化吲哚酮衍生物的合成

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

图式26. 三氟甲磺酸酐参与N-芳基丙烯酰胺的三氟甲基芳化

Scheme 26. Trifluoromethylarylation of N-arylacrylamides involving triflic anhydride

图式27. 三氟乙酸酐参与N-芳基丙烯酰胺的三氟甲基芳化

Scheme 27. Trifluoromethylarylation of N-arylacrylamides involving TFAA

图式28. 三氟甲基磺酰氯的光解用于N-芳基丙烯酰胺的三氟甲基芳化

Scheme 28. Photohomolysis of CF3SO2Cl for N-arylacrylamides trifluoromethylarylation

图式29. 溴代二氟乙酸乙酯参与的自由基串连反应

Scheme 29. Radical tandem reaction involving ehyl bromodifluoroacetate

图式30. 可见光介导的二氟甲基化吲哚酮衍生物的合成

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

图式31. 二氟乙酸用于二氟甲基化的吲哚酮衍生物的合成

Scheme 31. Difluoroacetic acid for the synthesis of difluoromethyl oxindoles

图式32. 三氟甲基芳烃的选择性单一碳氟键活化

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

图式33. 三氟甲基酮的选择性单一碳氟键活化

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

图式34. 光介导的三氟乙酸乙酯的选择性碳氟键活化

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

图式35. 光介导的磺酰化吲哚酮衍生物的合成

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

图式36. 可见光诱导的三组分反应

Scheme 36. Visible-light-induced three components reactions

图式37. 可见光介导的磺酸盐和磺酰胺的选择性合成

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

图式38. 可见光诱导的单氟甲基磺酰化吲哚酮衍生物的合成

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

图式39. 芳基重氮盐参与的自由基串连反应

Scheme 39. Radical tandem reactions involving aryl diazonium salts

图式40. 杂芳基卤化物参与3,3-二取代吲哚酮衍生物的合成

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

图式41. N-芳基丙烯酰胺的三氯甲基芳化

Scheme 41. Trichloromethylarylation of N-arylacrylamides

图式42. 羟烷基吲哚酮衍生物的合成

Scheme 42. Synthesis of hydroxyalkyl oxindoles

图式43. 无光催化剂和添加剂的三氟甲基化吲哚酮衍生物的合成

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

图式44. 质子偶合电子转移允许的N-芳基丙烯酰胺的氢芳化

Scheme 44. PCET enabled hydroarylation of N-arylacrylamides

图式45. 钴光氧化还原双催化的烯烃分子内氢芳化

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

图式46. 电荷转移复合物介导的烯烃分子内氢芳化反应

Scheme 46. CTC mediated hydroarylation of N-arylacrylamides

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