铜(II)配合物催化Chan-Lam偶联反应研究进展

doi:10.6023/cjoc202203034

摘要/Abstract

铜催化的Chan-Lam偶联反应是一种高效构建C—N、C—O和C—S键的重要方法, 具有条件温和、底物范围广及产率高等优点, 在有机合成、药物化学和材料科学等领域有着广泛的应用. 虽然有大量铜盐或铜盐/配体组合催化的Chan-Lam反应被报道, 但具有明确分子结构铜(II)配合物催化的Chan-Lam反应研究相对较少. 近年来, 含不同配体铜(II)配合物催化的Chan-Lam反应吸引了合成化学家们的关注, 取得了一定的成就. 一部分结构新颖的铜配合物被设计合成出来, 并用作芳基硼酸与多种亲核体Chan-Lam偶联反应的催化剂. 从均相催化和异相催化两方面综述了铜配合物催化Chan-Lam偶联反应的最新研究进展, 均相催化部分按铜配合物配位方式的不同加以分类, 非均相催化部分按时间先后予以阐述, 并对不同课题组提出的Chan-Lam偶联反应机理进行了梳理分析, 最后展望了该研究领域的未来发展前景.

关键词: 铜(II)配合物, 芳基硼酸, 亲核体, Chan-Lam偶联, N-芳基化

Copper-catalyzed Chan-Lam reaction represents an important and highly efficient method for the synthesis of organic molecules containing carbon-heteroatom (C—N, C—O, C—S) bonds, which has many advantages such as mild conditions, wide substrates range and high yields. Therefore, the Chan-Lam coupling reactions are extensively applied in organic synthesis, medicinal chemistry and material science, etc. Although many catalytic systems using different copper salt alone or in combination with various ligands for Chan-Lam coupling reaction have been extensively reported by different groups, the studies on the Chan-Lam coupling reaction employing well-defined copper complexes as catalysts were underdeveloped. In recent years, the Chan-Lam reactions catalyzed by copper complexes with different ligands have attracted more special attention from synthetic chemist and made many achievements. Some novel copper complexes have been designed and synthesized, which were further used as efficient catalysts for Chan-Lam coupling reactions of arylboronic acids with various nucleophiles. The recent progresses on Chan-Lam coupling reactions catalyzed by well-defined copper(II) complexes are summarized from two aspects of homogeneous catalysis and heterogeneous catalysis in detail. Then the homogeneous Chan-Lam reactions are classified by the different coordination mode of copper complexes, and the heterogeneous Chan-Lam reactions are described according to chronological order. The reaction mechanism on Chan-Lam coupling proposed by different research groups is also straightened out and discussed. Finally, the development prospects of this research field are pointed out.

Key words: copper(II) complex, arylboronic acid, nucleophile, Chan-Lam coupling, N-arylation

引用此文

贾雪锋, 仝向娟. 铜(II)配合物催化Chan-Lam偶联反应研究进展[J]. 有机化学, 2022, 42(9): 2640-2658.

Xuefeng Jia, Xiangjuan Tong. Recent Progress on Chan-Lam Coupling Reactions Catalyzed by Copper(II) Complexes[J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2640-2658.

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图/表 41

图式1. 铜催化的Chan-Lam偶联反应

Scheme 1. Copper-catalyzed Chan-Lam coupling reaction

图式2. [Cu(OH)•TMEDA]2Cl2催化芳基硼酸与含氮杂环的C—N偶联

Scheme 2. [Cu(OH)•TMEDA]2Cl2-catalyzed C—N coupling of arylboronic acids with nitrogen-containing heterocycles

图式3. [Cu(DMAP)4I]I催化芳基/烷基硼酸与含氮、硫亲核体的C—N和C—S偶联

Scheme 3. [Cu(DMAP)4I]I-catalyzed C—N and C—S coupling of aryl/alkylboronic acids with nitrogen- and sulfur-containing nucleophiles

图式4. 1,4-氮杂丁二烯衍生铜配合物催化芳基硼酸与芳香胺的C—N偶联和芳香醛与硝基烷烃的Nitroaldol反应

Scheme 4. 1,4-Diazabutadiene-derived copper complexes-catalyzed C—N coupling of arylboronic acids with aromatic amines and Nitroaldol reactions between arylaldehydes and nitroalkanes

图式5. 1,10-邻菲啰啉骨架铜(II)配合物的制备及其催化芳基硼酸与咪唑衍生物的C—N偶联

Scheme 5. Preparation of copper complexes with 1,10-phen- anthroline skeleton and its catalytic C—N coupling of arylboronic acids with 1H-imidazole derivatives

图式6. 铜(II)-Salen配合物催化芳基硼酸与芳香胺、咪唑衍生物的C—N偶联

Scheme 6. Cu(II)-Salen complexes-catalyzed C—N coupling of arylboronic acids with aromatic amines or 1H-imidazole derivatives

图式7. N,O-配位铜(II)配合物催化芳基硼酸与胺、咪唑衍生物的C—N偶联

Scheme 7. N,O-Coordinated copper(II) complexes-catalyzed C—N coupling of arylboronic acids with aromatic amines or 1H-imidazole derivatives

图式8. 磺酸酯-亚胺铜(II)配合物催化苯硼酸与胺、咪唑衍生物的C—N偶联

Scheme 8. Sulfoato-imine copper(II) complex-catalyzed C—N coupling of phenylboronic acids with amines or 1H-imidazole derivatives

图1. 含不同阴离子N,N,O-配位铜(II)配合物的结构

Figure 1. Structures of N,N,O-coordinated copper(II) complexes with different anions

图2. 水杨醛衍生不同骨架和配位方式的铜(II)配合物

Figure 2. Copper complexes with different structure and coordination mode derived from salicylaldehyde

图式9. 带正电荷双核铜(II)配合物催化芳基硼酸与胺的C—N偶联

Scheme 9. Dinuclear positively charged copper(II) complex-catalyzed C—N coupling of arylboronic acids with amines

图式10. 氮杂环卡宾铜(II)配合物催化芳基硼酸与胺的C—N偶联

Scheme 10. NHC-Cu(II)-catalyzed C—N coupling of arylboronic acids with amines

图式11. 倍半硅氧烷铜(II)配合物催化芳基硼酸与含不同取代基苯甲酸的C—O偶联

Scheme 11. Cu(II)-silsesquioxanes-catalyzed C—O coupling of arylboronic acids with different substituted benzoic acids

图式12. fac-[Ir(ppy)3]/醋酸铜协同催化芳基硼酸与芳香胺的C—N偶联

Scheme 12. fac-[Ir(ppy)3]/Cu(OAc)2 dual-catalyzed C—N coupling of arylboronic acids with aromatic amines

图式13. 可见光/醋酸铜协同催化的Chan-Lam偶联/[3+2]环加成串联反应

Scheme 13. Photoredox/Cu(OAc)2 dual-catalyzed Chan-Lam coupling and [3+2] cycloaddition cascade reaction

图式14. 可见光/铜催化下NH-二芳基砜亚胺与芳基硼酸的C—N偶联

Scheme 14. Photoredox/copper dual-catalyzed C—N coupling of NH-diaryl sulfoximines with arylboronic acids

图式15. Fe3O4-EDTA-Cu(II)催化芳基硼酸与胺的C—N偶联

Scheme 15. Fe3O4-EDTA-Cu(II)-catalyzed C—N coupling of arylboronic acids with amines

图式16. Cu/MCIP-1催化芳基硼酸与芳香胺的C—N偶联

Scheme 16. Cu/MCIP-1-catalyzed C—N coupling of arylboronic acids with aromatic amines

图式17. 铜(II)-席夫碱配合物催化芳基硼酸与胺的C—N偶联

Scheme 17. Cu(II)-Schiff base complex-catalyzed C—N coupling of arylboronic acids with amines

图式18. Cu(tpa)-MOF催化芳基硼酸与咪唑衍生物的C—N偶联

Scheme 18. Cu(tpa)-MOF-catalyzed C—N coupling of arylboronic acids with 1H-imidazole derivatives

图式19. MCM-41-1,10-Phen-CuSO4催化芳基硼酸与硫醇的 C—S偶联

Scheme 19. MCM-41-1,10-Phen-CuSO4-catalyzed C—S coupling of arylboronic acids with thiols

图式20. Cu2(BDC)2(BPY)-MOF催化芳基硼酸与芳香胺的 C—N偶联

Scheme 20. Cu2(BDC)2(BPY)-MOF-catalyzed C—N coupling of arylboronic acids with aromatic amines

图式21. Cu@PI-COF催化芳基硼酸与胺的C—N偶联

Scheme 21. Cu@PI-COF-catalyzed C—N coupling of arylboronic acids with amines

图式22. Cu(OAc)2@TpBpy催化芳基硼酸与咪唑的C—N偶联

Scheme 22. Cu(OAc)2@TpBpy-catalyzed C—N coupling of arylboronic acids with 1H-imidazole

图式23. Pd1Cu1@12DA-STS催化芳基硼酸与胺的C—N偶联

Scheme 23. Pd1Cu1@12DA-STS-catalyzed C—N coupling of arylboronic acids with amines

图式24. Cu-ACP-Am-Fe3O4@SiO2催化芳基硼酸与芳香伯胺的C—N偶联

Scheme 24. Cu-ACP-Am-Fe3O4@SiO2-catalyzed C—N coupling of arylboronic acids with aromatic primary amines

图式25. Cu(II)@MMT催化芳基硼酸与咪唑衍生物的C—N偶联

Scheme 25. Cu(II)@MMT-catalyzed C—N coupling of arylboronic acids with 1H-imidazole derivatives

图式26. POVCF 1催化芳基硼酸与胺的C—N偶联

Scheme 26. POVCF 1-catalyzed C—N coupling of arylboronic acids with amines

图式27. Cu@KF-C/MFe2O4催化芳基硼酸与胺、咪唑的C—N偶联

Scheme 27. Cu@KF-C/MFe2O4-catalyzed C—N coupling of arylboronic acids with amines and 1H-imidazole derivatives

图式28. 蓝光照射下Cu/P-C3N4催化芳基硼酸与吡啶-2-胺的C—N偶联

Scheme 28. Cu/P-C3N4-catalyzed C—N coupling of arylboronic acids with pyridine-2-amines under the irradiation of blue light

图式29. CuCl2@PANPA-2F催化芳基硼酸与对甲苯磺酰叠氮、咪唑衍生物的C—N偶联

Scheme 29. CuCl2@PANPA-2F-catalyzed C—N coupling of arylboronic acids with amines with tosyl azide or 1H-imidazole derivatives

图式30. Evans提出的初步反应机理

Scheme 30. Initial mechanistic possibilities proposed by Evans

图式31. Chan和Lam提出的倾向于三价铜中间体的反应途径

Scheme 31. Reaction pathway favoring Cu(III) intermediate proposed by Chan and Lam

图式32. Collman提出的[Cu(OH)•TMEDA]2Cl2催化Chan- Lam反应机理

Scheme 32. Collman's proposed mechanism on Chan-Lam reaction catalyzed by [Cu(OH)•TMEDA]2Cl2

图式33. Stahl提出的Chan-Lam醚化反应机理

Scheme 33. Stahl's proposed mechanism on Chan-Lam etherification reaction

图式34. Watson提出的Chan-Lam胺化反应机理

Scheme 34. Watson's proposed mechanism on Chan-Lam amination reaction

图式35. Schaper提出的磺酸酯亚胺铜配合物催化Chan-Lam反应机理

Scheme 35. Schaper's proposed mechanism on Chan-Lam reaction catalyzed by Sulfonato-imino copper(II) complexes

图式36. 双核铜配合物19a催化Chan-Evans-Lam偶联反应的可能机理

Scheme 36. Proposed mechanism of Chan-Evans-Lam coupling reaction catalyzed by dinuclear copper(II) complex 19a

图式37. fac-[Ir(ppy)3]/醋酸铜协同催化Chan-Lam偶联反应的机理

Scheme 37. Mechanism of Chan-Lam coupling reaction catalyzed by fac-[Ir(ppy)3]/Cu(OAc)2

图式38. 可见光/醋酸铜协同催化的Chan-Lam偶联/[3+2]环加成串联反应的机理

Scheme 38. Mechanism of Chan-Lam coupling and [3+2] cycloaddition cascade reaction catalyzed by photoredox/Cu(OAc)2

图式39. NH-二芳基砜亚胺与芳基硼酸的自催化光氧化还原Chan-Lam偶联反应的机理

Scheme 39. Mechanism of Autocatalytic photoredox Chan-Lam coupling of free diaryl sulfoximines with arylboronic acids

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