Application of Covalent Organic Framework Materials as Heterogeneous Ligands in Organic Synthesis

doi:10.6023/cjoc202107030

Abstract

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

Cite this article

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.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 30

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

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

Scheme 3. Synthesis of CuII-TRIPTA

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

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

Scheme 6. Synthesis of Cu@T-D COF

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

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

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

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

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

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

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

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

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

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

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

Scheme 18. Synthesis of Pd@Bpy COF

Scheme 19. Heck reaction catalyzed by Pd@Bpy COF

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

Scheme 21. Cyclization reaction catalyzed by Ag@TpTta

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

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

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

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

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

Scheme 27. Synthesis of Pt@COF

Scheme 28. Photohydrodebromination of bromo-derivatives

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

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

References 58

[1]	Lu, L. F.; Zou, S. H.; Fang, B. Z. ACS Catal. 2021, 11, 6020. doi: 10.1021/acscatal.1c00903
[2]	Peng, L. F.; Hu, Z. F.; Lu, Q. C.; Tang, Z. L.; Jiao, Y. C.; Xu, X. H. Chin. Chem. Lett. 2019, 30, 2151. doi: 10.1016/j.cclet.2019.05.063
[3]	Li, J. X.; Du, Z. X.; Pan, Q. Y.; Zhang, L. L.; Liu, D. L. Inorg. Chim. Acta 2020, 509, 119677. doi: 10.1016/j.ica.2020.119677
[4]	Chen, M. N.; Mo, L. P.; Cui, Z. S.; Zhang, Z. H. Curr. Opin. Green Sustainable Chem. 2019, 15, 27.
[5]	Sankar, M.; He, Q.; Engel, R. V.; Sainna, M. A.; Logsdail, A. J.; Roldan, A.; Willock, D. J.; Agarwal, N.; Kiely, C. J.; Hutchings, G. J. Chem. Rev. 2020, 120, 3890. doi: 10.1021/acs.chemrev.9b00662
[6]	Geng, K.; He, T.; Liu, R.; Dalapati, S.; Tan, K. T.; Li, Z.; Tao, S.; Gong, Y.; Jiang, Q.; Jiang, D. Chem. Rev. 2020, 120, 8814. doi: 10.1021/acs.chemrev.9b00550
[7]	Liu, Y.; Zhou, W.; Teo, W. L.; Wang, K.; Zhang, L.; Zeng, Y.; Zhao, Y. Chem 2020, 6, 3172. doi: 10.1016/j.chempr.2020.08.021
[8]	Rodriguez-San-Miguel, D.; Montoro, C.; Zamora, F. Chem. Soc. Rev. 2020, 49, 2291. doi: 10.1039/C9CS00890J
[9]	Chen, X. Y.; Geng, K. Y.; Liu, R. Y.; Tan, K. T.; Gong, Y. F.; Li, Z. P.; Tao, S. S.; Jiang, Q. H.; Jiang, D. L. Angew. Chem., nt. Ed. 2020, 59, 5050.
[10]	Zhang, A. R.; Ai, Y. J. Prog. Chem. 2020, 32, 1564. (in Chinese)
	(张安睿, 艾玥洁, 化学进展, 2020, 32, 1564.) doi: 10.7536/PC200202
[11]	Wei, X.; Chen, J.; Guan, M.; Qiu, H.-D. Chin. J. Anal. Chem. 2019, 47, 1721. (in Chinese)
	(魏欣, 陈佳, 关明, 邱洪灯, 分析化学, 2019, 47, 1721.)
[12]	Yu, G.; Wang, C. Chin. J. Org. Chem. 2020, 40, 1437. (in Chinese) doi: 10.6023/cjoc202003018
	(于歌, 汪成, 有机化学, 2020, 40, 1437.) doi: 10.6023/cjoc202003018
[13]	Fang, J.; Zhao, W. J.; Zhang, M. H.; Fang, Q. R. Acta Chim. Sinica 2021, 79, 186. (in Chinese) doi: 10.6023/A20100471
	(方婧, 赵文娟, 张明浩, 方千荣, 化学学报, 2021, 79, 186.) doi: 10.6023/A20100471
[14]	Fu, J. R.; Ben, T. Acta Chim. Sinica 2020, 78, 805. (in Chinese) doi: 10.6023/A20040128
	(付静茹, 贲腾, 化学学报, 2020, 78, 805.) doi: 10.6023/A20040128
[15]	Wang, T.; Xue, R.; Wei, Y. L.; Wang, M. Y.; Guo, H.; Yang, W. Prog. Chem. 2018, 30, 753. (in Chinese)
	(王婷, 薛瑞, 魏玉丽, 王明玥, 郭昊, 杨武, 化学进展, 2018, 30, 753.) doi: 10.7536/PC171012
[16]	Jiang, C. H.; Feng, X.; Wang, B. Acta Chim. Sinica 2020, 78, 466. (in Chinese) doi: 10.6023/A20030088
	(蒋成浩, 冯霄, 王博, 化学学报, 2020, 78, 466.) doi: 10.6023/A20030088
[17]	Peng, Z. K.; Ding, H. M.; Chen, R. F.; Gao, C.; Wang, C. Acta Chim. Sinica 2019, 77(8), 681. (in Chinese) doi: 10.6023/A19040118
	(彭正康, 丁慧敏, 陈如凡, 高超, 汪成, 化学学报, 2020, 78, 681.)
[18]	Hou, C.; Chen, W. Q.; Fu, L. H.; Zhang, S. F.; Liang, C. Prog. Chem. 2020, 32, 895. (in Chinese) doi: 10.7536/PC191226
	(侯晨, 陈文强, 付琳慧, 张素风, 梁辰, 化学进展, 2020, 32, 895.) doi: 10.7536/PC191226
[19]	Lan, X. W.; Bai, G. Y. Prog. Chem. 2020, 32, 1482. (in Chinese)
	(兰兴旺, 白国义, 化学进展, 2020, 32, 1482.) doi: 10.7536/PC200204
[20]	Esrafili, A.; Wagner, A.; Inamdar, S.; Acharya, A. P. Adv. Health-care Mater. 2021, 10, 2002090.
[21]	Zeng, J. Y.; Wang, X. S.; Xie, B. R.; Li, M. J.; Zhang, X. Z. Angew. Chem., nt. Ed. 2020, 59, 10087.
[22]	Zhao, X.; Pachfule, P.; Thomas, A. Chem. Soc. Rev. 2021, 50, 6871. doi: 10.1039/D0CS01569E
[23]	Yang, Q.; Luo, M. L.; Liu, K. W.; Cao, H. M.; Yan, H. J. Appl. Catal., 2020, 276, 119174. doi: 10.1016/j.apcatb.2020.119174
[24]	Lopez-Magano, A.; Jimenez-Almarza, A.; Aleman, J.; Mas-Balleste, R. Catalysts 2020, 10, 720. doi: 10.3390/catal10070720
[25]	Li, L.; Li, P. F.; Wang, B. Chem. J. Chin. Univ. 2020, 41, 1917. (in Chinese)
	(李丽, 李鹏飞, 王博, 高等学校化学学报, 2020, 41, 1917.)
[26]	Wang, H.; Wang, H.; Wang, Z.; Tang, L.; Zeng, G.; Xu, P.; Chen, M.; Xiong, T.; Zhou, C.; Li, X.; Huang, D.; Zhu, Y.; Wang, Z.; Tang, J. Chem. Soc. Rev. 2020, 49, 4135. doi: 10.1039/d0cs00278j pmid: 32421139
[27]	Guo, L. P.; Jin, S. B. ChemPhotoChem 2019, 3, 973. doi: 10.1002/cptc.v3.10
[28]	Zhao, S. Y.; Liu, C.; Xu, H.; Yang, X. B. Prog. Chem. 2020, 32, 274. (in Chinese)
	(赵苏艳, 刘畅, 徐浩, 杨晓博, 化学进展, 2020, 32, 274.) doi: 10.7536/PC190602
[29]	Wei, P. F.; Qi, M. Z.; Wang, Z. P.; Ding, S. Y.; Yu, W.; Liu, Q.; Wang, L. K.; Wang, H. Z.; An, W. K.; Wang, W. J. Am. Chem. Soc. 2018, 140, 4623. doi: 10.1021/jacs.8b00571
[30]	Liu, J. G.; Wang, N.; Ma, L. L. Chem. Asian J. 2020, 15, 338. doi: 10.1002/asia.v15.3
[31]	Sharma, R. K.; Yadav, P.; Yadav, M.; Gupta, R.; Rana, P.; Srivastava, A.; Zboril, R.; Varma, R. S.; Antonietti, M.; Gawande, M. B. Mater. Horiz. 2020, 7, 411. doi: 10.1039/C9MH00856J
[32]	Zhi, Y. F.; Wang, Z. R.; Zhang, H. L.; Zhang, Q. C. Small 2020, 16, 2001070. doi: 10.1002/smll.v16.24
[33]	Fan, M. Y.; Wang, W. D.; Zhu, Y. Y.; Sun, X.; Zhang, F. W.; Dong, Z. P. Appl. Catal., 2019, 257, 117942. doi: 10.1016/j.apcatb.2019.117942
[34]	Cheng, H. Y.; Wang, T. Adv. Synth. Catal. 2021, 363, 144. doi: 10.1002/adsc.v363.1
[35]	Guo, J.; Jiang, D. L. ACS Cent. Sci. 2020, 6, 869. doi: 10.1021/acscentsci.0c00463
[36]	Duan, X. Y.; Liu, N.; Wang, J.; Ma, J. Y. Chin. J. Org. Chem. 2019, 39, 661. (in Chinese)
	(段希焱, 刘宁, 王佳, 马军营, 有机化学, 2019, 39, 661.) doi: 10.6023/cjoc201808015
[37]	Han, Y.; Zhang, M.; Zhang, Y. Q.; Zhang, Z. H. Green Chem. 2018, 20, 4891. doi: 10.1039/C8GC02611D
[38]	Di, J. Q.; Zhang, M.; Chen, Y. X.; Wang, J. X.; Geng, S. S.; Tang, J. Q.; Zhang, Z. H. Green Chem. 2021, 23, 1041. doi: 10.1039/D0GC03400B
[39]	Liu, H. S.; Yu, Z. Q.; Sun, Z. C.; Wang, Y.; Liu, Y. Y.; Wang, A. J. Chem. J. Chin. Univ. 2020, 41, 1091. (in Chinese)
	(刘恒烁, 遇治权, 孙志超, 王瑶, 刘颖雅, 王安杰, 高等学校化学学报, 2020, 41, 1091.)
[40]	Das, S. K.; Krishna Chandra, B.; Molla, R. A.; Sengupta, M.; Islam, S. M.; Majee, A.; Bhaumik, A. Mol. Catal. 2020, 480, 110650.
[41]	Chakraborty, D.; Nandi, S.; Mullangi, D.; Haldar, S.; Vinod, C. P.; Vaidhyanathan, R. ACS Appl. Mater. Interfaces 2019, 11, 15670. doi: 10.1021/acsami.9b02860
[42]	Gao, T.; Su, X.; Xu, H.; Hu, H.; Zeng, C.; Gao, Y. ChemistrySelect 2020, 5, 15010. doi: 10.1002/slct.v5.47
[43]	Mu, M. M.; Wang, Y. W.; Qin, Y. T.; Yan, X. L.; Li, Y.; Chen, L. G. ACS Appl. Mater. Interfaces 2017, 9, 22856. doi: 10.1021/acsami.7b05870
[44]	Sarkar, S.; Ghosh, S.; Mondal, J.; Islam, S. M. Chem Commun. 2020, 56, 12202. doi: 10.1039/D0CC04835F
[45]	Kan, X.; Wang, J. C.; Kan, J. L.; Shang, J. Y.; Qiao, H.; Dong, Y. B. Inorg. Chem. 2021, 60, 3393. doi: 10.1021/acs.inorgchem.0c03783
[46]	Han, Y.; Di, J. Q.; Zhao, A. D.; Zhang, Z. H. Appl. Organomet. Chem. 2019, 33, e5172.
[47]	Sun, Q.; Wu, C.; Pan, Q.; Zhang, B.; Liu, Y.; Lu, X.; Sun, J.; Sun, L.; Zhao, Y. ChemNanoMat 2020, 7, 95. doi: 10.1002/cnma.v7.1
[48]	Liu, J.; Zhan, H.; Wang, N.; Song, Y.; Wang, C.; Wang, X.; Ma, L.; Chen, L. ACS Appl. Nano Mater. 2021, 4, 6239. doi: 10.1021/acsanm.1c01038
[49]	Pachfule, P.; Panda, M. K.; Kandambeth, S.; Shivaprasad, S. M.; Díaz, D. D.; Banerjee, R. J. Mater. Chem. A 2014, 2, 7944. doi: 10.1039/C4TA00284A
[50]	Han, J.; Sun, X.; Wang, X.; Wang, Q.; Hou, S.; Song, X.; Wei, Y.; Wang, R.; Ji, W. Org. Lett. 2020, 22, 1480. doi: 10.1021/acs.orglett.0c00061
[51]	Zhang, J. Q.; Peng, Y. S.; Leng, W. G.; Gao, Y. A.; Xu, F. F.; Chai, J. L. Chin. J. Catal. 2016, 37, 468. doi: 10.1016/S1872-2067(15)61050-6
[52]	Vardhan, H.; Pan, Y.; Yang, Z.; Verma, G.; Nafady, A.; Al-Enizi, A. M.; Alotaibi, T. M. APL Mater. 2019, 7, 101111. doi: 10.1063/1.5122674
[53]	Ghosh, S.; Khan, T. S.; Ghosh, A.; Chowdhury, A. H.; Haider, M. A.; Khan, A.; Islam, S. M. ACS Sustainable Chem. Eng. 2020, 8, 5495. doi: 10.1021/acssuschemeng.9b06704
[54]	Pachfule, P.; Kandambeth, S.; Diaz Diaz, D.; Banerjee, R. Chem. Commun. 2014, 50, 3169. doi: 10.1039/C3CC49176E
[55]	Vardhan, H.; Verma, G.; Ramani, S.; Nafady, A.; Al-Enizi, A. M.; Pan, Y.; Yang, Z.; Yang, H.; Ma, S. ACS Appl. Mater. Interfaces 2019, 11, 3070. doi: 10.1021/acsami.8b19352
[56]	Cifuentes, J. M. C.; Ferreira, B. X.; Esteves, P. M.; Buarque, C. D. Top. Catal. 2018, 61, 689. doi: 10.1007/s11244-018-0910-9
[57]	Fan, M. Y.; Wang, W. D.; Zhu, Y. Y.; Sun, X.; Zhang, F. W.; Dong, Z. P. Appl. Catal., 2019, 257, 119027.
[58]	Leng, W.; Ge, R.; Dong, B.; Wang, C.; Gao, Y. RSC Adv. 2016, 6, 37403. doi: 10.1039/C6RA05304A

共价有机框架材料作为非均相配体在有机合成中的应用