钴催化C(sp2)—H活化构建苯并含氮杂环骨架的研究进展

doi:10.6023/cjoc202404038

摘要/Abstract

苯并含氮杂环化合物是天然产物、药物活性分子中的重要骨架. 近年来, 过渡金属催化作为C(sp²)—H活化反应的有力手段, 在苯并含氮杂环化合物的合成中有着重要贡献. 在绿色环保经济的理念下, 地球含量丰富的钴作为廉价金属催化剂逐渐进入研究人员的视野. 归纳总结了2015年至今国内外钴催化C(sp²)—H活化构建苯并含氮杂环结构的研究进展, 使用的钴催化剂按种类可分为环戊二烯(Cp)配位的CpCo(III)催化剂以及无Cp配位的Co(II)催化剂, 按反应类型可分为分子间反应和分子内反应, 从这几个方面进行系统综述, 并对该领域目前的局限和未来发展进行了总结与展望.

关键词: 钴催化剂, C(sp²)—H活化, 环化反应, 苯并含氮杂环, 过渡金属催化

Nitrogen-containing benzo heterocycles serve as crucial scaffolds in natural products and biologically active molecules. In recent years, transition metal catalysis has emerged as a powerful strategy in C(sp²)—H activation, making significant contributions to the synthesis of nitrogen-containing benzo heterocycles. Embracing the concept of green and sustainable economy, the abundantly available cobalt metal is gaining attention as an economical catalyst among researchers. In this review, the research progress on cobalt-catalyzed C(sp²)—H activation for the construction of nitrogen-containing benzo heterocycles from 2015 to present is summarized. The cobalt catalysts used can be classified into cyclopentadienyl (Cp)-coordinated CpCo(III) catalysts as well as Cp-free Co(II) catalysts by species, and reaction types can be categorized into intermolecular and intramolecular reactions, which are systematically reviewed according to these classifications. Furthermore, the current limitations and future prospects of this field are summarized and discussed.

Key words: cobalt catalysts, C(sp²)—H activation, cyclization reactions, nitrogen-containing benzo heterocycles, transition metal catalysis

引用此文

田勋, 邓国刚, 羊晓东. 钴催化C(sp²)—H活化构建苯并含氮杂环骨架的研究进展[J]. 有机化学, 2025, 45(2): 655-667.

Xun Tian, Guogang Deng, Xiaodong Yang. Progress on Cobalt-Catalyzed C(sp²)—H Activation for the Construction of Nitrogen-Containing Benzo Heterocycles[J]. Chinese Journal of Organic Chemistry, 2025, 45(2): 655-667.

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图/表 39

图1. 含有苯并含氮杂环结构的天然产物及药物分子

Figure 1. Natural products and pharmaceutical molecules containing nitrogen-containing benzo heterocyclic structures

图式1. CpCo催化的分子间C(sp2)—H活化成环机理

Scheme 1. Mechanism of CpCo-catalyzed intermolecular C(sp2)—H activation for ring formation

图式2. 肟与炔烃合成多取代异喹啉

Scheme 2. Multi-substituted isoquinolines synthesis from oximes and alkynes

图式3. 酰基苯胺与炔烃合成多取代喹啉

Scheme 3. Multi-substituted quinolines synthesis from acylaniline and alkynes

图式4. 苯胺衍生物与炔烃合成吲哚化合物

Scheme 4. Indoles synthesis from aniline derivatives and alkynes

图式5. 苯基亚胺与二噁唑酮合成苯并嘧啶化合物

Scheme 5. Benzo-pyrimidines synthesis from imine substrates and dioxazolones

图式6. N-氯代苯甲酰胺与炔烃合成异喹啉酮

Scheme 6. Isoquinolinones synthesis from N-chlorobenzamide and alkynes

图式7. 苯磺酰亚胺与二噁唑酮合成噻二嗪硫氧化物

Scheme 7. Thiadiazine sulfoxides synthesis from benzenesulfo- nimides and dioxazolones

图式8. 苯甲酰亚胺酸酯与碳酸乙烯亚乙酯合成二氢异喹啉

Scheme 8. Dihydroisoquinolines synthesis from benzimidates and vinylethylene carbonates

图式9. N-氯代苯甲酰胺与烯烃不对称合成二氢异喹啉酮

Scheme 9. Asymmetric synthesis of dihydroisoquinolinones from N-chlorobenzamide and olefins

图式10. 硫叶立德氧化物和苯并噁唑合成吲哚并吲哚酮

Scheme 10. Indoloindolones synthesis from sulfoxonium ylides and anthranils

图式11. 苯磺酰亚胺与二噁唑酮不对称合成噻二嗪硫氧化物

Scheme 11. Asymmetric synthesis of thiadiazine sulfoxides from benzenesulfonimides and dioxazolones

图式12. 苯胺衍生物与丙烯酸酯合成2-酰基吲哚啉

Scheme 12. 2-Acylindolines synthesis from aniline derivatives and acrylates

图式13. 裸露苯甲酰胺与噁二唑酮合成喹唑啉酮

Scheme 13. Quinazolinones synthesis from primary amides and oxadiazolones

图式14. N-氯代苯甲酰胺与醋酸乙烯酯合成异喹啉酮

Scheme 14. Isoquinolinones synthesis from N-chlorobenza- mides and vinyl acetate

图式15. N-氯代苯甲酰胺与硅基乙烯合成4-硅基取代二氢异喹啉酮

Scheme 15. 4-Silicon substituted dihydroisoquinolinones synthesis from N-chlorobenzamide and silicon substituted olefins

图式16. 叠氮甲酸酯分子内酰胺化合成苯并环氨基甲酸酯

Scheme 16. Benzocyclic carbamates synthesis by intramolecular amidation from azidocarbonates

图式17. 二噁唑酮内酰胺化合成苯并内酰胺

Scheme 17. Benzofused lactam synthesis by intramolecular amidation from dioxazolones

图式18. 二噁唑酮内酰胺化合成苯并内酰胺

Scheme 18. Benzofused lactam synthesis by intramolecular amidation from dioxazolones

图式19. Co(II)催化的分子间C(sp2)—H活化成环反应

Scheme 19. Co(II)-catalyzed intermolecular ring-forming reactions through C(sp2)—H activation

图式20. 碱与溶剂调控的区域选择性合成异喹啉酮与异吲哚酮

Scheme 20. Base- and solvent-modulated regioselective synthesis of isoquinolinones and isoindolones

图式21. 甲酰胺与乙烯/乙炔气体合成多环内酰胺

Scheme 21. Multicyclic lactams synthesis from formamides and ethylene/acetylene gas

图式22. 苯甲酰胺与联烯合成多取代异喹啉酮

Scheme 22. Multisubstituted isoquinolinones synthesis from benzamides and allenes

图式23. 苯甲酰肼与异氰或一氧化碳合成3-亚胺基异吲哚啉酮及邻苯二甲酰亚胺

Scheme 23. 3-Iminoisoindolinones and phthalimides synthesis from benzoylhydrazine and isocyanides or carbon monoxide

图式24. 苯甲酰胺/丙烯酰胺与炔烃合成异喹啉酮/吡啶酮

Scheme 24. Isoquinolones/pyridinones synthesis from benza- mide/acrylamide and alkynes

图式25. 苯甲酰胺/丙烯酰胺与端炔合成异喹啉酮/吡啶酮

Scheme 25. Isoquinolones/pyridinones synthesis from benza- mide/acrylamide and terminal alkynes

图式26. 苯甲酰胺与马来酰亚胺合成螺环化合物

Scheme 26. Spirocycles synthesis from benzamides and maleimides

图式27. 苯甲酰胺与重氮化合物化学选择性合成螺环产物

Scheme 27. Chemoselective spirocycles synthesis from benzamide and diazo compounds

图式28. 萘胺与羟胺酯合成萘并咪唑

Scheme 28. Naphthoimidazole synthesis from naphthylamines and hydroxylamine esters

图式29. Salox*配体的简便易得合成

Scheme 29. Facile and accessible synthesis of Salox* ligands

图式30. 芳基磷酰胺与炔烃合成膦手性六元环磷酰胺

Scheme 30. Synthesis of P-stereo-genic hexacyclophosphamide by aryl phosphamides and alkynes

图式31. 苯甲酰胺与烯烃不对称合成手性二氢异喹啉酮

Scheme 31. Asymmetric synthesis of chiral dihydroisoquinolinones from benzamides and olefins

图式32. 苯甲酰胺/磷酰胺与联烯不对称合成手性含氮杂环

Scheme 32. Asymmetric synthesis of chiral nitrogen-containing heterocycles from benzamide/phosphoramidites and allenes

图式33. 苯甲酰胺与炔烃/烯烃不对称合成轴手性异喹啉衍生物

Scheme 33. Asymmetric synthesis of axially chiral isoquinoline derivatives from benzamide and alkynes/olefins

图式34. 苯甲酰胺与联烯/烯烃/异氰不对称合成轴手性异喹啉/异吲哚酮衍生物

Scheme 34. Asymmetric synthesis of axially chiral isoquinolines/isoindolones derivatives by benzamide and allenes/olefins/ isocyanines

图式35. 芳基磺酰胺与联烯/炔烃不对称合成N-轴手性的苯并内磺酰胺

Scheme 35. Asymmetric synthesis of N-axially chiral benzolactosulfonamides from aryl sulfonamides and allenes/alkynes

图式36. 苄胺衍生物与炔烃的对映选择性C—H/N—H环化反应

Scheme 36. Enantioselective C—H/N—H cyclization of benzylamine derivatives with alkynes

图式37. 苯甲酰胺与炔烃合成N-轴手性异喹啉酮

Scheme 37. Asymmetric synthesis of N-axially chiral isoquinolinones by benzamides and alkynes

图式38. 苯甲酰胺与炔烃分子内合成双轴手性多环产物

Scheme 38. Intramolecular synthesis of biaxial chiral polycyclic products from benzamides and alkynes

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钴催化C(sp²)—H活化构建苯并含氮杂环骨架的研究进展

Progress on Cobalt-Catalyzed C(sp²)—H Activation for the Construction of Nitrogen-Containing Benzo Heterocycles

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