共价有机框架材料作为非均相配体在有机合成中的应用

doi:10.6023/cjoc202107030

摘要/Abstract

共价有机框架材料(covalent organic frameworks, COFs)是一类由轻质元素(C、O、N、B等)通过共价键构成的新型结晶多孔材料. 由于其具有高比表面积、高孔隙率、高结晶度, COFs具有其它传统材料无法比拟的优点. COFs作为非均相配体负载金属离子能够实现不同类型的催化反应, 且催化剂能够重复使用. 总结了COFs作为非均相配体负载不同金属离子催化的有机反应最新研究进展.

关键词: 共价有机框架材料, 多相催化, 有机合成, 非均相配体

Covalent organic frameworks (COFs) are a new type of crystalline porous material composed of light elements (C, O, N, B, etc.) through covalent bonds. Because of its high specific surface area, high porosity, and high crystallinity, COFs have advantages that other traditional materials can not match. By using COFs as heterogeneous ligands to support metal ions, different types of catalytic reactions can be realized, and the catalyst can be reused. The latest research progress of COFs as heterogeneous ligands supporting different metal ions to catalyze various organic reactions is summarized.

Key words: covalent organic framework materials, heterogeneous catalysis, organic synthesis, heterogeneous ligands

引用此文

陈育萱, 陈奇, 张占辉. 共价有机框架材料作为非均相配体在有机合成中的应用[J]. 有机化学, 2021, 41(10): 3826-3843.

Yuxuan Chen, Qi Chen, Zhanhui Zhang. Application of Covalent Organic Framework Materials as Heterogeneous Ligands in Organic Synthesis[J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 3826-3843.

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图/表 30

图式1. Cu(OAc)2@TpBpy的合成

Scheme 1. Synthesis of Cu(OAc)2@TpBpy

图式2. Cu(OAc)2@TpBpy催化Chan-Lam偶联反应可能机理

Scheme 2. Plausible reaction mechanism for Chan-Lam coupling reaction catalyzed by Cu(OAc)2@TpBpy

图式3. CuII-TRIPTA合成

Scheme 3. Synthesis of CuII-TRIPTA

图式4. CuII-TRIPTA催化苯硼酸偶联反应合成联芳基化合物

Scheme 4. CuII-TRIPTA catalyzed synthesis of biaryl compounds by coupling reaction of phenylboronic acid

图式5. Cu@COF催化Glaser-Hay偶联反应

Scheme 5. Glaser-Hay coupling catalyzed by Cu@COF

图式6. Cu@T-D COF的合成

Scheme 6. Synthesis of Cu@T-D COF

图式7. Cu@T-D COF催化炔-叠氮化物点击反应

Scheme 7. Cu@T-D COF catalyzed alkyne-azide click reaction

图式8. Cu@COFHX催化选择性烯烃氧化

Scheme 8. Selective oxidation of olefins catalyzed by Cu@COFHX

图式9. Cu@COF-BD(OH)2的合成

Scheme 9. Synthesis of Cu@COF-BD(OH)2

图式10. Cu@COF-BD(OH)2催化的的环化反应

Scheme 10. Cyclization reaction catalyzed by Cu@COF-BD(OH)2

图式11. Cu(II)@COF-DM的合成

Scheme 11. Synthesis of Cu(II)@COF-DM

图式12. Cu(II)@COF-DM催化合成烯丙基胺

Scheme 12. Synthesis of allylamine catalyzed by Cu(II)@COF-DM

图式13. Pd@COF催化的Suziki-Miyaura偶联反应

Scheme 13. Suziki-Miyaura coupling reaction catalyzed by Pd@COF

图式14. Pd@TPM-3D-COF-BPY的合成

Scheme 14. Synthesis of Pd@TPM-3D-COF-BPY

图式15. Pd(0)@TpPa-1催化 Sonogashira 偶联反应

Scheme 15. Pd(0)@TpPa-1 catalyzes Sonogashira coupling reaction

图式16. Pd(0)/COF-BTDH的合成

Scheme 16. Synthesis of Pd(0)/COF-BTDH

图式17. Pd/COF-BTDH催化的Heck反应

Scheme 17. Heck reaction catalyzed by Pd/COF-BTDH

图式18. Pd@Bpy COF的合成

Scheme 18. Synthesis of Pd@Bpy COF

图式19. Pd@Bpy COF催化的Heck反应

Scheme 19. Heck reaction catalyzed by Pd@Bpy COF

图式20. Ircod(I)@Py-2,2'-BPyPh COF催化合成苯基硼酸酯

Scheme 20. Synthesis of phenyl boronate catalyzed by Ircod(I)- @Py-2,2'-BPyPh COF

图式21. Ag@TpTta催化的环化反应

Scheme 21. Cyclization reaction catalyzed by Ag@TpTta

图式22. Au(0)@TpPa-1催化硝基苯酚还原

Scheme 22. Au(0)@TpPa-1 catalyzed nitrophenol reduction

图式23. VO-TAPT-2,3-DHTA的合成

Scheme 23. Synthesis of VO-TAPT-2,3-DHTA

图式24. VO-TAPT-2,3-DHTA催化Prins反应和硫化物氧化

Scheme 24. VO-TAPT-2,3-DHTA catalyzed Prins reaction and sulﬁde oxidation

图式25. FeCl3@TPB-DMTP-COF的合成

Scheme 25. Synthesis of FeCl3@TPB-DMTP-COF

图式26. FeCl3@TPB-DMTP-COF催化的肉桂酸的脱羧氧化交叉偶联反应

Scheme 26. FeCl3@TPB-DMTP-COF-catalyzed decarboxylation oxidative cross-coupling reaction of cinnamic acid

图式27. Pt@COF的合成

Scheme 27. Synthesis of Pt@COF

图式28. 溴代衍生物的光加氢脱溴

Scheme 28. Photohydrodebromination of bromo-derivatives

图式29. Mn/Pd@Py-2,2'-BPyPh的合成

Scheme 29. Synthesis of Mn/Pd@Py-2,2'-BPyPh

图式30. Mn/Pd@Py-2,2'-BPyPh催化Heck-环氧化串联反应

Scheme 30. Mn/Pd@Py-2,2'-BPyPh catalyzed Heck-epoxidation tandem reaction

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