过渡金属催化吲哚的串联去芳构化反应研究进展

doi:10.6023/cjoc202210026

摘要/Abstract

吲哚啉类化合物广泛存在于天然产物、药物和生物活性分子中, 其结构多样性构建具有重要的意义. 目前, 吲哚的去芳构化转化已成为构建螺环、稠环、多取代吲哚啉类化合物的原子和步骤经济性途径. 近年来, 吲哚的去芳构化反应得到了不断发展, 但对于C(2)=C(3)环内烯烃的串联去芳构化转化研究仍有较大的发展空间. 基于此, 聚焦迁移插入与自由基串联策略, 详细总结了Pd、Ni、Co和Cu过渡金属催化的吲哚串联去芳构化转化, 并探讨了相关的反应机理以及发展趋势.

关键词: 过渡金属催化, 吲哚, 去芳构化, 迁移插入, 自由基串联

Indolines are prevalent scaffolds of numerous natural products, pharmaceutical agents, and bioactive molecules, therefore, various strategies have been developed to access indolines. Indole dearomatization has been recognized as an important and straightforward strategy for constructing diverse functionalized indolines. Among a multitude of indoles dearomatization, the well-known strategies have relied on the inherent nucleophilicity of indole, while migratory insertion strategies for dearomatization have been widely applied in recent years. Herein, the recent advances of Pd, Ni, Co, Cu-catalyzed tandem dearomatizations of indoles via migratory insertion and radical-mediated process are summarized detailedly, and the mechanism and development tendency of this dearomatization reactions are discussed.

Key words: transition-metal-catalysis, indoles, dearomatization, migratory insertion, radical process

引用此文

庞明杨, 常宏宏, 冯璋, 张娟. 过渡金属催化吲哚的串联去芳构化反应研究进展[J]. 有机化学, 2023, 43(4): 1271-1291.

Mingyang Pang, Honghong Chang, Zhang Feng, Juan Zhang. Recent Advances in Transition-Metal-Catalyzed Tandem Dearomatization of Indoles[J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1271-1291.

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图/表 33

图1. 部分具有生物活性的吲哚啉类化合物

Figure 1. Examples of bioactive molecules containing indoline structure

图式1. 过渡金属催化的吲哚的主要去芳构化模式

Scheme 1. Typical established approaches for indole dearomatization

图式2. Pd催化吲哚的分子内不对称去芳构化转化

Scheme 2. Pd-catalyzed intramolecular enantioselective dearomatization of indole

图式3. Pd催化下吲哚的分子间去芳构化Heck反应

Scheme 3. Pd-catalyzed dearomatization of indole derivatives via intermolecular Heck reactions

图式4. Pd-催化C(2)-取代吲哚的分子内去芳构化还原Heck反应

Scheme 4. Pd-catalyzed intramolecular dearomative reductive-Heck reaction of C(2)-substituted indoles

图式5. 钯催化苯硫脂的脱羰去芳构化反应

Scheme 5. Pd-catalyzed decarbonylative dearomative reaction of thioesters

图式6. Pd-催化吲哚的双芳基去芳构化反应

Scheme 6. Pd-catalyzed dearomative diarylation of indoles

图式7. 钯催化吲哚的双官能团去芳构化反应

Scheme 7. Palladium-catalyzed dearomative difunctionalization of indoles

图式8. Pd-催化吲哚的Heck/Sonogashira反应

Scheme 8. Pd-catalyzed Heck/Sonogashira reaction of indoles

图式9. Pd-催化去芳构化芳基烷氧基与芳基磷酸酯化反应

Scheme 9. Pd-catalyzed dearomative aryloxylation and arylphosphorylation of indoles

图式10. Pd催化吲哚的去芳构化芳基烯基反应

Scheme 10. Pd-catalyzed dearomative arylvinylation reaction of indoles

图式11. Pd催化吲哚的插羰去芳构化反应

Scheme 11. Pd-catalyzed carbonylative dearomatization of indoles

图式12. Pd催化吲哚的去芳构化芳基/环亚胺化反应

Scheme 12. Pd-catalyzed dearomative aryl/cycloimidoylation of indoles

图式13. Pd(0)-催化吲哚的顺式2,3-芳基硼酯化去芳构化反应

Scheme 13. Pd(0)-catalyzed directed syn-1,2-carboboration of indoles

图式14. Pd(II)-催化吲哚的氧化去芳构化反应

Scheme 14. Pd(II)-catalyzed oxidative dearomatization of indoles

图式15. Pd催化吲哚的螺环化去芳构化反应

Scheme 15. Pd-catalyzed spirocyclization dearomatization of indoles

图式16. Pd-催化吲哚的氨基去芳构化反应

Scheme 16. Pd-catalyzed amination/dearomatization reaction of indoles

图式17. Pd/PC-Phos催化吲哚的不对称去芳构化反应

Scheme 17. Pd/PC-Phos-catalyzed asymmetric dearomatization of indole

图式18. Pd催化吲哚的不对称环化异构化反应

Scheme 18. Pd-catalyzed enantioselective cycloisomerization reaction of indoles

图式19. 钯催化基于吲哚C(3)亲核性的去芳构化转化

Scheme 19. Pd-catalyzed dearomatization of indoles via C(3)-nucleophilicity

图式20. Ni催化吲哚的不对称还原Heck环化反应

Scheme 20. Ni-catalyzed asymmetric reductive Heck cyclization of indoles

图式21. Ni催化吲哚的非对映选择性去芳构化碳碘化反应

Scheme 21. Ni-catalyzed diastereoselective dearomative carboiodination reaction of indoles

图式22. Ni催化吲哚的去芳构化芳基硼酯化反应

Scheme 22. Ni-catalyzed dearomative arylboration of indoles

图式23. Co催化吲哚的转移氢化去芳构化反应

Scheme 23. Co-catalyzed dearomatization of indoles via transfer hydrogenation

图式24. Cu催化吲哚的芳基去芳构化反应

Scheme 24. Cu-catalyzed arylation dearomatization of indoles

图式25. Cu催化吲哚的分子间不对称去芳构化反应

Scheme 25. Cu-Catalyzed intermolecular asymmetric dearomatization of indole

图式26. Cu催化吲哚的有氧氧化去芳构化反应

Scheme 26. Cu-catalyzed aerobic oxidative dearomatization of indoles

图式27. Cu催化吲哚衍生物的2,3-双叠氮化反应

Scheme 27. Cu-catalyzed diastereoselective 2,3-diazidation of indoles

图式28. Cu催化吲哚与二氧化碳的三氟甲基去芳构化反应

Scheme 28. Cu-catalyzed radical trifluoromethylative dearomatization of indoles with CO2

图式29. Cu催化吲哚的对映选择性硼酯去芳构化反应

Scheme 29. Cu-catalyzed enantioselective borylative dearomatization of indoles

图式30. Cu催化吲哚的非对映选择性碳硼酯去芳构化转化

Scheme 30. Cu-catalyzed diastereoselective dearomative carboborylation of indoles

图式31. Cu催化吲哚的不对称去芳构化硼酯化反应

Scheme 31. Copper-catalyzed asymmetric dearomative borylation of indoles

图式32. Cu催化吲哚的不对称去芳构化硅基化反应

Scheme 32. Cu-catalyzed asymmetric dearomative silylation of indoles

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