Research Progress of Chan-Lam Coupling Reaction in Heterogeneous Catalysis

doi:10.6023/cjoc202203038

Abstract

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

Cite this article

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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Fig. & Tab. 38

Figure 1. Inorganic material supported metal catalyst

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

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

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

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

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

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

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

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

Scheme 7. Chan-Lam reaction catalyzed by CuFAP

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

Figure 4. Graphene supported metal catalyst

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

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

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

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

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

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

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

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

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

Figure 5. Polymer supported metal catalyst

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

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

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

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

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

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

Figure 7. Carbene metal complex catalyst

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

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

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

Scheme 25. Chan-Lamreaction catalyzed by CuI-NHC

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

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

Figure 9. Schiff base complex catalyst

Scheme 28. Chan-Lam reaction catalyzed by complex C3

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

References 72

[1]	Ullmann, F. Ber. Dtsch. Chem. Ges. 1903, 36, 2382. doi: 10.1002/cber.190303602174
[2]	Goldberg, I. Ber. Dtsch. Chem. Ges. 1906, 39, 1691. doi: 10.1002/cber.19060390298
[3]	Paul, F.; Patt, J.; Hartwig, J. F. J. Am. Chem. Soc. 1994, 116, 5969. doi: 10.1021/ja00092a058
[4]	Guram, A. S.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 7901. doi: 10.1021/ja00096a059
[5]	Chan, D. M. T.; Monaco, K. L.; Wang, R. P. Tetrahedron Lett. 1998, 39, 2933. doi: 10.1016/S0040-4039(98)00503-6
[6]	Lam, P.; Clark, C. G.; Saubern, S.; Adams, J.; Combs, A. J. Tetrahedron Lett. 1998, 39, 2941.
[7]	Evans, D. A.; Katz, J. L.; West, T. R. Tetrahedron Lett. 1998, 39, 2937. doi: 10.1016/S0040-4039(98)00502-4
[8]	Cheng, G.; Luo, M. Eur. J. Org. Chem. 2011, 2519.
[9]	Ma, X.; Liu, F.; Mo, D. Chin. J. Org. Chem. 2017, 37, 1069. (in Chinese) doi: 10.6023/cjoc201702001
	(马小盼, 刘凤萍, 莫冬亮, 有机化学, 2017, 37, 1069.) doi: 10.6023/cjoc201702001
[10]	Duan, X.; Liu, N.; Wang, J.; Ma, J. 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
[11]	Zhang, Y.; Zhang, M.; Yang, J; Ding, L.; Xu, J.; Xiong, S. Nanoscale 2016, 8, 15978. doi: 10.1039/C6NR05078F
[12]	Tian, Z.; Li, Q.; Yan, L.; Ai, S. Catal. Commun. 2015, 61, 97. doi: 10.1016/j.catcom.2014.12.019
[13]	Jain, S. L.; Rana, B. S.; Singh, B.; Sinha, A. K.; Bhaumik, A.; Nandi, M.; Sain, B. Green Chem. 2010, 12, 374. doi: 10.1039/b917382j
[14]	Ganai, A. K.; Bhardwaj, R.; Hotha, S. New J. Chem. 2010, 34, 2662. doi: 10.1039/c0nj00292e
[15]	Sharma, H.; Mahajan, H.; Jamwal, B.; Paul, S. Catal. Commun. 2018, 107, 68. doi: 10.1016/j.catcom.2018.01.016
[16]	Jamwal, B.; Kaur, M.; Sharma, H.; Khajuria, C.; Paul, S.; Clark, J. H. New J. Chem. 2019, 43, 4919. doi: 10.1039/C8NJ05050C
[17]	Sandip, P.; Vibhute, P. M.; Mhaldar, D. S.; Gaikwad, R. V.; Shejwal, D. M. Monatsh. Chem. 2020, 151, 87. doi: 10.1007/s00706-019-02529-w
[18]	Sharma, C.; Sharma, N.; Sharma, S.; Sharma, S.; Paul, S. Curr. Res. Green Sustainable Chem. 2021, 4, 100133. doi: 10.1016/j.crgsc.2021.100133
[19]	Garnier, T.; Sakly, R.; Danel, M.; Chassaing, S.; Pale, P. Synthesis 2016, 48, 1223.
[20]	You, C.R.; Yao, F.; Yan, T.; Cai, M. Z. RSC Adv. 2016, 6, 43605. doi: 10.1039/C6RA04298H
[21]	Kantam, M. L.; Gopaldasu, T.; Venkanna, C. S. J. Org. Chem. 2006, 71, 9522. doi: 10.1021/jo0614036
[22]	Sarmah, M.; Dewan, A.; Boruah, P. K.; Das, M. R.; Bora, U. Appl. Organomet. Chem. 2020, 34, 1.
[23]	Lee, C.; Wei, X.; Kysar, J. W. Science 2008, 321, 385. doi: 10.1126/science.1157996
[24]	Georgakilas, V.; Otyepka, M.; Bourlinos, A. B. Chem. Rev. 2012, 112, 6156. doi: 10.1021/cr3000412 pmid: 23009634
[25]	Mittal, A.; Kumari, S.; Parmanand; Yadav, D.; Sharma, S. K. Appl. Organomet. Chem. 2019, 34, 1.
[26]	Seyedi, N.; Nejad, M. S.; Saidi, K.; Sheibani, H. Appl. Organomet. Chem. 2019, 23, 527. doi: 10.1002/aoc.1565
[27]	Sharma, N.; Choudhary, A.; Kaur, M.; Sharma, C.; Paul, S.; Gupta, M. RSC Adv. 2020, 10, 30048. doi: 10.1039/D0RA01540G
[28]	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
[29]	Yaghi, O. M.; Li, G.; Li, H. Nature 1995, 378, 703. doi: 10.1038/378703a0
[30]	Côté, A. P.; Benin, A. I.; Ockwig, N. W.; O'Keeffe, M.; Matzger, A. J.; Yaghi, O. M. Science 2005, 310, 1166. doi: 10.1126/science.1120411
[31]	Dinga, S. Y.; Wang, W. Chem. Soc. Rev. 2013, 42, 548. doi: 10.1039/C2CS35072F
[32]	Asiri, A. M.; Garcia, H. Chem. Soc. Rev. 2015, 44, 1922. doi: 10.1039/C4CS00254G
[33]	Antonietti, M.; Thomas, A.; Fernando, M.; Guillermo, C. Angew. Chem., Int. Ed. 2008, 47, 3450. doi: 10.1002/anie.200705710
[34]	Campbell, N. L.; Clowes, R.; Ritchie, L. K. Chem. Mater. 2009, 21, 204. doi: 10.1021/cm802981m
[35]	Khosravi, A.; Mokhtari, J.; Naimi-Jamal, M. R.; Tahmasebi, S.; Panahi, L. RSC Adv. 2017, 7, 46022. doi: 10.1039/C7RA09772G
[36]	Han, Y.; Zhang, M.; Zhang, Y. Q.; Zhang, Z. H. Green Chem. 2018, 20, 4891. doi: 10.1039/C8GC02611D
[37]	Muoz, A.; Leo, P.; Orcajo, G.,; Martínez, F.; Calleja, G. ChemCatChem. 2019, 11, 3376. doi: 10.1002/cctc.201900906
[38]	Qian,. W. Z.; He,. Y. F.; Wang,. J. F.; Chen,. J.; Wang,. R. M. Chin. Poly. Bull. 2017, 4, 1. (in Chinese)
	(钱文珍, 何玉凤, 王建凤, 陈静, 王荣民, 高分子通报, 2017, 4, 1.)
[39]	Chen, X.; Chen, C. X.; Peng, J. S. Chin. J. Org. Chem. 2021, 41, 1319 (in Chinses). doi: 10.6023/cjoc202007063
	(陈鑫, 陈春霞, 彭进松, 有机化学, 2021, 41, 1319.) doi: 10.6023/cjoc202007063
[40]	Choi, C. Y.; Nam, J. P.; Nah, J. W. J. Ind. Eng. Chem. 2016, 33, 1.
[41]	Jeremic, S.; Djokic, L.; Ajdai, V.; Boinovi, N.; Nikodinovic-Runic, J.; Opsenica, L. Int. J. Biol. Macromol. 2019, 129, 351. doi: S0141-8130(18)34921-3 pmid: 30710586
[42]	Sharma, S.; Kaur, M., Sharma, C.; Choudhary, A.; Paul, S. ACS Omega. 2021, 6, 19529. doi: 10.1021/acsomega.1c01830
[43]	Seyedi, N.; Zahedifar, M. Appl. Organomet. Chem. 2021, 35, e6364.
[44]	Mugemana, C.; Fustin, C. A.; Gohy, J. F. Macromol. Rapid. Commun. 2013, 34, 962. doi: 10.1002/marc.201300214
[45]	Schmidt, J.; Weber, J.; Epping, J. D. Adv. Mater. 2009, 21, 702. doi: 10.1002/adma.200802692
[46]	Gary, C. H.; Chiang; Thomas, O. Org. Lett. 2004, 6, 3079. pmid: 15330592
[47]	Islam, M.; Mondal, S.; Mondal, P.; Roy, A. S.; Tuhina, K.; Mobarok, M. Catal. Lett. 2011, 141, 1171. doi: 10.1007/s10562-011-0606-2
[48]	Zhang, C.; Zhu, H.; Gang, K.; Tao, M.; Zhang, W.; Ma, N. React. Funct. Polym. 2021, 160, 104831. doi: 10.1016/j.reactfunctpolym.2021.104831
[49]	Collman, J. P.; Zhong, M. Org. Lett. 2000, 2, 1233. pmid: 10810715
[50]	Hay, A. S. J. Org. Chem. 1962, 27, 3320. doi: 10.1021/jo01056a511
[51]	Onaka, T.; Umemoto, H.; Miki, Y.; Nakamura, A.; Maegawa, T. J. Org. Chem. 2014, 79, 6703. doi: 10.1021/jo500862t
[52]	Subhasish, R.; Manas, J. S.; Bishwapran, K.; Phukan, P. Chem. Commun. 2016, 52, 1170. doi: 10.1039/C5CC04619J
[53]	Jia, X. F.; Peng, P.; Cui, J.; Xin, N. N.; Huang, X. Q. Asian J. Org. Chem. 2018, 7, 1093. doi: 10.1002/ajoc.201800153
[54]	Correa, A.; Martin, R. Angew. Chem., Int. Ed. 2009, 48, 6201. doi: 10.1002/anie.200900667
[55]	Ohishi, T.; Nishiura, M.; Hou, Z. Angew. Chem.,Int. Ed. 2008, 47, 5792. doi: 10.1002/anie.200801857
[56]	Liu, J.; Zhang, R.; Wang, S.; Sun, W.; Xia, C. Org. Lett. 2009, 11, 1321. doi: 10.1021/ol9001027
[57]	Martin, D.; Kehrli, S.; Augustin, M.; Clavier, H.; Mauduit, M.; Alexakis, A. J. Am. Chem. Soc. 2006, 128, 8416. pmid: 16802804
[58]	Gajare, S.; Jagadale, M.; Naikwade, A.; Bansode, P.,; Rashinkar, G. Appl. Organometal Chem. 2019, 33, e4915. doi: 10.1002/aoc.4915
[59]	Cope, J. D.; Sheridan, P. E.; Galloway, C. J.; Awoyemi, R. F.; Emerson, J. P. Organometallics 2020, 39, 4457. doi: 10.1021/acs.organomet.0c00552
[60]	Zhang, M. Y.; Xu, Z. B.; Shi, D. B. Tetrahedron 2021, 79, 131861. doi: 10.1016/j.tet.2020.131861
[61]	Hie, L.; Fine, N. N. F.; Shah, T. K.; Baker, E. L.; Hong, X.; Yang, Y. F.; Liu, P.; Houk, K. N.; Garg, N. K. Nature 2015, 524, 79. doi: 10.1038/nature14615
[62]	Sergeev, A. G.; Hartwig, J. F. Science 2011, 332, 439. doi: 10.1126/science.1200437 pmid: 21512027
[63]	Ando, S.; Hirota, Y.; Matsunaga, H.; Ishizuka, T.M. Tetrahedron Lett. 2019, 60, 1277. doi: 10.1016/j.tetlet.2019.04.004
[64]	Velusamy, S.; Punniyamurthy, T. Eur. J. Org. Chem. 2003, 3913.
[65]	Kaboudin, B.; Abedi, Y.; Yokomatsu, T. Eur. J. Org. Chem. 2011, 6656.
[66]	Sarmah, G.; Dewan, A.; Bora, U. Tetrahedron Lett. 2014, 55, 31. doi: 10.1016/j.tetlet.2013.10.084
[67]	Sun, W.; Xia, C. G.; Wang, H. W. New J. Chem. 2002, 226, 755.
[68]	Xue, L.; Zhou, D. J.; Tang, L. React. Funct. Polym. 2004, 58, 117. doi: 10.1016/j.reactfunctpolym.2003.10.003
[69]	Hu, D. D.; Cui, Y. L.; Dong, X. L. React. Funct. Polym. 2001, 48, 201. doi: 10.1016/S1381-5148(01)00053-0
[70]	Shweta, K.; Devendra, D. P. Tetrahedron Lett. 2015, 56, 4135. doi: 10.1016/j.tetlet.2015.05.049
[71]	Kumar, A.; Layek, S.; Agrahari, B.; Kujur, S.; Pathak, D. D. ChemistrySelect 2019, 4, 1337. doi: 10.1002/slct.201803113
[72]	Akatyev, N.; Kudryavtsev, K.; Belokon, Y. ChemCatChem. 2020, 12, 3010. doi: 10.1002/cctc.202000212

多相催化体系下Chan-Lam偶联反应的研究进展