多相催化体系下Chan-Lam偶联反应的研究进展

doi:10.6023/cjoc202203038

摘要/Abstract

作为C—N键的经典构筑方式, 最近Chan-Lam偶联反应的研究取得了长足发展, 反应体系更加温和绿色, 特别是多相催化体系相关研究, 为催化剂的性能提升、回收和重复使用奠定了基础. 从催化剂载体和有机配体的设计、合成及性能研究出发, 综述了近年来负载型和配位型多相催化剂在Chan-Lam偶联反应中的应用.

关键词: Chan-Lam偶联反应, 多相催化, 含氮化合物, 胺化, C—N偶联

As a classical method of C—N bond formation, the research on Chan-Lam coupling has made great progress recently. The reaction system is more mild and green, especially the related research on heterogeneous catalytic system, which lays a foundation for the performance improvement, recovery and reuse of the catalyst. Starting from the design, synthesis and performance research of catalyst supporters and organic ligands, the application of supported and coordinated heterogeneous catalysts in Chan-Lam coupling reaction in recent years is summarized.

Key words: Chan-Lam coupling reaction, heterogeneous catalysis, nitrogen compound, amination, C—N coupling

引用此文

白瑞, 刘旭娟, 罗文钰, 刘珊珊, 焦林郁. 多相催化体系下Chan-Lam偶联反应的研究进展[J]. 有机化学, 2022, 42(8): 2342-2354.

Rui Bai, Xujuan Liu, Wenyu Luo, Shanshan Liu, Linyu Jiao. Research Progress of Chan-Lam Coupling Reaction in Heterogeneous Catalysis[J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2342-2354.

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图/表 38

图1. 无机材料负载金属催化剂

Figure 1. Inorganic material supported metal catalyst

图式1. Cu@Fe3O4-TiO2-L-dopa催化的Chan-Lam偶联反应

Scheme 1. Chan-Lam reaction catalyzed by Cu@Fe3O4-TiO2-L- dopa

图式2. PdCu@12DA-STS催化的Chan-Lam偶联反应

Scheme 2. Chan-Lam reaction catalyzed by PdCu@12DA-STS

图式3. Cu-ACP-Am-Fe3O4@SiO2催化的Chan-Lam偶联反应

Scheme 3. Chan-Lam reaction catalyzed by Cu-ACP-Am-Fe3O4 @SiO2

图2. Cu-ACP-Am-Fe3O4@SiO2的催化反应机理

Figure 2. Mechanism of Cu-ACP-Am-Fe3O4@SiO2 catalyst

图式4. Ni@Fe3O4-NDCs催化的Chan-Lam偶联反应

Scheme 4. Chan-Lam reaction catalyzed by Ni@Fe3O4-NDCs

图式5. CuI-USY催化的Chan-Lam偶联反应

Scheme 5. Chan-Lam reaction catalyzed by CuI-USY

图3. CuI-USY催化的Chan-Lam偶联反应中间体

Figure 3. Intermediate of Chan-Lam reaction catalyzed by CuI-USY

图式6. MCM-41-L-proline-CuCl催化的Chan-Lam偶联反应

Scheme 6. Chan-Lam reaction catalyzed by MCM-41-L- proline-CuCl

图式7. CuFAP催化的Chan-Lam偶联反应

Scheme 7. Chan-Lam reaction catalyzed by CuFAP

图式8. CuII@MMT催化的Chan-Lam偶联反应

Scheme 8. Chan-Lam reaction catalyzed by CuII@MMT

图4. 石墨烯材料负载金属催化剂

Figure 4. Graphene supported metal catalyst

图式9. AP/L-Cu@GO催化偶联反应

Scheme 9. AP/L-Cu@GO catalyzed coupling reaction

图式10. Cu@Ag-TiO2-NGO催化的Chan-Lam偶联反应

Scheme 10. Chan-Lam reaction catalyzed by Cu@Ag-TiO2- NGO

图式11. Cu/P-CN催化的Chan-Lam偶联反应

Scheme 11. Chan-Lam reaction catalyzed by Cu/P-CN

图式12. Cu2(BDC)2(BPY)-MOF催化的Chan-Lam偶联反应

Scheme 12. Chan-Lam reaction catalyzed by Cu2(BDC)2(BPY)- MOF

图式13. Cu@PI-COF催化的Chan-Lam偶联反应

Scheme 13. Chan-Lam reaction catalyzed by Cu@PI-COF

图式14. URJC-1-MOF催化的Chan-Lam偶联反应

Scheme 14. Chan-Lam reaction catalyzed by URJC-1-MOF

图式15. Cu/BCN催化的Chan-Lam偶联反应

Scheme 15. Chan-Lam reaction catalyzed by Cu/BCN

图式16. Cu@KF-C/NiFe2O4催化的Chan-Lam偶联反应

Scheme 16. Chan-Lam reaction catalyzed by Cu@KF-C/ NiFe2O4

图式17. CuONPs-P2-HA-CSN催化的Chan-Lam偶联反应

Scheme 17. Chan-Lam reaction catalyzed by CuONPs-P2- HA-CSN

图5. 聚合物负载金属催化剂

Figure 5. Polymer supported metal catalyst

图式18. Cu-PAR催化的Chan-Lam偶联反应

Scheme 18. Chan-Lam reaction catalyzed by Cu-PAR

图式19. CuCl2@PANPA-2F催化的Chan-Lam偶联反应

Scheme 19. Chan-Lam reaction catalyzed by CuCl2@PANPA-2F

图式20. [Cu(OH)TMEDA]2Cl2催化的Chan-Lam偶联反应

Scheme 20. Chan-Lam reaction catalyzed by [Cu(OH)- TMEDA]2Cl2

图6. [Cu(OH)TMEDA]2Cl2的催化机理

Figure 6. Mechanism of [Cu(OH)TMEDA]2Cl2 catalyst

图式21. [Cu(DMAP)4I]I催化的Chan-Lam偶联反应

Scheme 21. Chan-Lam reaction catalyzed by [Cu(DMAP)4I]I

图式22. 配位铜催化的Chan-Lam偶联反应

Scheme 22. Chan-Lam coupling reaction catalyzed by coordination copper

图7. 卡宾金属络合物催化剂

Figure 7. Carbene metal complex catalyst

图式23. Cu@[GrFemImi]NHC催化的Chan-Lam偶联反应

Scheme 23. Chan-Lam reaction catalyzed by Cu@[GrFemImi]- NHC

图式24. NHC-CuII催化的Chan-Lam偶联反应

Scheme 24. Chan-Lam reaction catalyzed by NHC-CuII

图8. NHC-CuII催化的Chan-Lam偶联反应机理

Figure 8. Mechanism of Chan-Lam reaction catalyzed by NHC-CuII

图式25. CuI-NHC催化的Chan-Lam偶联反应

Scheme 25. Chan-Lamreaction catalyzed by CuI-NHC

图式26. NHC-Ni催化的Chan-Lam偶联反应

Scheme 26. Chan-Lam reaction catalyzed by NHC-Ni

图式27. 铜络合物Cu-salen催化的Chan-Lam偶联反应

Scheme 27. Chan-Lam reaction catalyzed by copper complex Cu-salen

图9. 席夫碱络合物催化剂

Figure 9. Schiff base complex catalyst

图式28. 配合物C3催化的Chan-Lam偶联反应

Scheme 28. Chan-Lam reaction catalyzed by complex C3

图式29. AF-SB-Cu@GO催化的Chan-Lam偶联反应

Scheme 29. Chan-Lam reaction catalyzed by AF-SB-Cu@GO

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