Recent Progress in Synthesis of Polysubstituted Imidazoles by Cyclization Reaction

doi:10.6023/cjoc202107014

Abstract

Imidazoles are a class of very important 5-memeric nitrogen-containing heterocyclic compounds, which have a wide range of applications in organic synthetic chemistry. They are widely found in natural products, applied drugs, materials and other fields, and are also a class of important organic synthesis intermediates. Therefore, the synthetic method of imidazole has attracted much attention. The recent progress in the synthesis of polysubstituted imidazoles by cyclization reaction is summarized. These methods and research progress of the synthesis of imidazoles from oxime esters, 2H-azacyclopropenes, ketones, 2-aminopyridines, azides, triazoles, alkynes, isothiocyanates, aromatic amines, amidines and nitriles are reviewed. Finally, the prospects of the reaction with this reagent are also proposed.

Key words: imidazole, cyclization, synthesis, research process

Cite this article

Mina Zhao, Zimo Yang, Desuo Yang. Recent Progress in Synthesis of Polysubstituted Imidazoles by Cyclization Reaction[J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 111-128.

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Fig. & Tab. 61

Figure 1. Some important imidazoles

Scheme 1. Synthesis of imidazole from oxime acetates and vinyl azides

Scheme 2. Plausible mechanism for the synthesis of imidazole from ketoxime acetates and tetrahydroisoquinolines

Scheme 3. Synthesis of imidazole from N-phenyl amidoxime esters

Scheme 4. Plausible mechanism for the synthesis of imidazole from benzimidates and 2H-azirines

Scheme 5. Plausible mechanism for the synthesis of imidazole with nitrones and 2H-azirines

Scheme 6. Synthesis of imidazole from 2-chloropyridines and 2H-azirines

Scheme 7. Synthesis of imidazole from o-phenylenediamines and β-diketones

Scheme 8. Synthesis of imidazole from 2-amino-1,3,5-triazines with 1,3-dicarbonyl compounds

Scheme 9. Synthesis of imidazole from 1,2 diketone

Scheme 10. Synthesis of imidazole from α-methylene ketone, benzaldehyde and NH4OAc

Scheme 11. Synthesis of imidazole from α-methylene ketone and aldehydes

Scheme 12. Synthesis of imidazole from benzylamines and aryl ketones

Scheme 13. Synthesis of imidazole from aryl ketones and aldehyde

Scheme 14. Plausible mechanism for the synthesis of imidazole from aryl methyl ketones, 2-aminobenzyl alcohols and TosMIC

Scheme 15. Synthesis of imidazole from aryl ketones, benzylamine and amine

Scheme 16. Synthesis of imidazole from chalcones and amine

Scheme 17. Synthesis of imidazole from 2-aminopyridine and ketones

Scheme 18. Synthesis of imidazole from 2-aminopyridines and aldehydes

Scheme 19. Synthesis of imidazole from 1,3-dicarbonyls and 2-aminopyridines

Scheme 20. Plausible mechanism for the synthesis of imidazole from benzimidamides and vinyl azides

Scheme 21. Synthesis of imidazole from propargylazide derivatives, isocyanates and amines

Scheme 22. Synthesis of imidazole from phenacyl azides with L-proline

Scheme 23. Synthesis of imidazole from aryl azides and TosMIC

Scheme 24. Synthesis of imidazole from vinyl azides and cyanamide

Scheme 25. Synthesis of imidazole from vinyl azides and imines

Scheme 26. Synthesis of imidazole from nitrile and N-(per)- fluoroalkyl-1,2,3-triazoles

Scheme 27. Plausible mechanism for the synthesis of imidazole from amines, alkynes and TMSN3

Scheme 28. Synthesis of imidazole from oxadiazolones with ynamides

Scheme 29. Synthesis of imidazole from alkyne, 2-amino-N- heterocycle, benzyl or allylic bromide

Scheme 30. Synthesis of imidazole from alkyne and 2-amino- pyridine

Scheme 31. Synthesis of imidazole from N-pyridinyl sulfilimines and ynamide

Scheme 32. Plausible mechanism for the synthesis of imidazole from alkynes, nitriles and tBuOK

Scheme 33. Plausible mechanism for the synthesis of imidazole from aryl isothiocyanates

Scheme 34. Synthesis of imidazole from primary alcohol and o-phenylenediamines

Scheme 35. Synthesis of imidazole from o-phenylenediamines

Scheme 36. Plausible mechanism for the synthesis of imidazole from o-nitroanilines and alcohols

Scheme 37. Synthesis of imidazole from o-phenylenediamines and D-glucose

Scheme 38. Synthesis of imidazole from o-phenylenediamines and benzonitriles

Scheme 39. Synthesis of imidazole from amidines

Scheme 40. Plausible mechanism for the synthesis of imidazole from N-phenylbenzamidine with phenylacetaldehyde

Scheme 41. Synthesis of imidazole from alkynylbenziodoxolones and amidoximes

Scheme 42. Synthesis of imidazole from amidines and ynals

Scheme 43. Synthesis of imidazole from amidines, ynals and alcohols, phenols, or water

Scheme 44. Synthesis of imidazole from amidines, ynals and carboxylic acids or amines

Scheme 45. Synthesis of imidazole from amidines, ynals and boronic acids

Scheme 46. Synthesis of imidazole from amidines, ynals and sodium sulfinates

Scheme 47. Synthesis of imidazole from amidines, ynals and water

Scheme 48. Plausible mechanism for the synthesis of imidazole from amides

Scheme 49. Synthesis of imidazole from glycine derivatives and 5-alkoxyoxazoles

Scheme 50. Synthesis of imidazole from N-alkyl enamines

Scheme 51. Synthesis of imidazolium salts from enamines and iodine

Scheme 52. Plausible mechanism for the synthesis of imidazole from enamines

Scheme 53. Synthesis of imidazole from enamines and amines

Scheme 54. Synthesis of imidazole from boronic acids and N- substituted-2-amino-acetonitriles

Scheme 55. Synthesis of imidazole from benzylamines and ntriles

Scheme 56. Synthesis of imidazole from azomethine ylides and isocyanides

Scheme 57. Synthesis of imidazole from isocyanides, 2,2,2- trifluorodiazoethane and activated methylene isocyanides or azomethine ylides

Scheme 58. Synthesis of imidazole from active methylene isocyanides and ketenimines

Scheme 59. Synthesis of imidazole from polycyclic aromatic azomethine ylides and nitriles

Scheme 60. Plausible mechanism for the synthesis of imidazole from amines and ClCF2COONa

References 78

[1]	(a) Roue, M.; Domart-Coulon, I.; Ereskovsky, A.; Djediat, C.; Perez, T.; Bourguet-Kondracki, M.-L. J. Nat. Prod. 2010, 73, 1277. doi: 10.1021/np100175x pmid: 23740514
	(b) Zhang, L.; Peng, X.-M.; Damu, G. L. V.; Geng, R.-X.; Zhou, C.-H. Med. Res. Rev. 2014, 34, 340. doi: 10.1002/med.21290 pmid: 23740514
[2]	(a) Tang, W.-Z.; Yang, Z.-Z.; Wu, W.; Tang, J.; Sun, F.; Wang, S.-P.; Cheng, C.-W.; Yang, F.; Lin, H.-W. J. Nat. Prod. 2018, 81, 894. doi: 10.1021/acs.jnatprod.7b01006
	(b) Zhao, K.; Yu, F.; Liu, W.; Huang, Y.; Said, A. A.; Li, Y.; Zhang, Q. J. Org. Chem. 2020, 85, 101. doi: 10.1021/acs.joc.9b02156
	(c) Qiu, Z.-P.; Tan, J.-H.; Cai, N.; Wang, K.; Ji, S.-M.; Huo, Y.-P. Chin. J. Org. Chem. 2019, 39, 679. (in Chinese) doi: 10.6023/cjoc201807007
	(邱志鹏, 谭继华, 蔡宁, 王凯, 籍少敏, 霍延平, 有机化学, 2019, 39, 679.) doi: 10.6023/cjoc201807007
[3]	Rohrig, U. F.; Majjigapu, S. R.; Chambon, M.; Bron, S.; Pilotte, L.; Colau, D.; Van den Eynde, B. J.; Turcatti, G.; Vogel, P.; Zoete, V.; Michielin, O. Eur. J. Med. Chem. 2014, 84, 284. doi: 10.1016/j.ejmech.2014.06.078
[4]	Perchellet, E. M.; Perchellet, J.-P.; Baures, P. W. J. Med. Chem. 2005, 48, 5955. pmid: 16161999
[5]	Atwell, G. J.; Fan, J.-Y.; Tan, K.; Denny, W. A. J. Med. Chem. 1998, 41, 4744. pmid: 9822545
[6]	Choi, J. Y.; Plummer, M. S.; Starr, J.; Desbonnet, C. R.; Soutter, H.; Chang, J.; Richard Miller, J.; Dillman, K.; Miller, A. A.; Roush, W. R. J. Med. Chem. 2012, 55, 852. doi: 10.1021/jm201349f
[7]	Vlahakis, J. Z.; Lazar, C.; Crandall, I. E.; Szarek, W. A. Bioorg. Med. Chem. 2010, 18, 6184.
[8]	Lee, J. C.; Laydon, J. T.; McDonnell, P. C.; Gallagher, T. F.; Kumar, S.; Green, D.; McNulty, D.; Blumenthal, M. J.; Richard Keys, J.; Land vatter, S. W.; Strickler, J. E.; McLaughlin, M. M.; Siemens, I. R.; Fisher, S. M.; Livi, G. P.; White, J. R.; Adams, J. L.; Young, P. R. Nature 1994, 372, 739. doi: 10.1038/372739a0
[9]	Hojabri, L.; Hartikka, A.; Moghaddam, F. M.; Arvidsson, P. I. Adv. Synth. Catal. 2007, 349, 740. doi: 10.1002/(ISSN)1615-4169
[10]	Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667. doi: 10.1021/cr010338r
[11]	Mao, P.; Yang, L.-R.; Xiao, Y.-M.; Yuan, J.-W.; Mai, W.-P.; Gao, J.; Zhang, X.-C. Chin. J. Org. Chem. 2019, 39, 443. (in Chinese) doi: 10.6023/cjoc201807008
	(毛璞, 杨亮茹, 肖咏梅, 袁金伟, 买文鹏, 高杰, 张心持, 有机化学, 2019, 39, 443.) doi: 10.6023/cjoc201807008
[12]	Hindi, K. M.; Panzner, M. J.; Tessier, C. A.; Cannon, C. L.; Youngs, W. J. Chem. Rev. 2009, 109, 3859. doi: 10.1021/cr800500u
[13]	Radziszewski, B. Ber. Dtsch. Chem. Ges. 1882, 15, 1493. doi: 10.1002/cber.v15:2
[14]	Zhao, X.-Y.; Ding, Y.-Y.; Lü, Y.-T.; Kang, C.-M. Chin. J. Org. Chem. 2019, 39, 1304. (in Chinese) doi: 10.6023/cjoc201809034
	(赵鑫雨, 丁扬扬, 吕英涛, 康从民, 有机化学, 2019, 39, 1304.)
[15]	Yang, K.; Yao, C.; Gao, J.-J.; Chen, S.-H.; Zheng, X.-J.; Deng, L.-X.; Zhang, Y.-N.; Liu, M.-J.; Wang, Z.-Y. Chin. J. Org. Chem. 2020, 40, 4168. (in Chinese) doi: 10.6023/cjoc202005074
	(杨凯, 姚辰, 高娟娟, 陈思鸿, 郑雪洁, 邓璐璇, 张毓娜, 刘美娟, 汪朝阳, 有机化学, 2020, 40, 4168.) doi: 10.6023/cjoc202005074
[16]	Xu, X.-M.; Chen, D.-M.; Wang, Z.-L. Chin. J. Org. Chem. 2019, 39, 3338. (in Chinese) doi: 10.6023/cjoc201904068
	(徐鑫明, 陈德茂, 王祖利, 有机化学, 2019, 39, 3338.) doi: 10.6023/cjoc201904068
[17]	Huang, H.; Ji, X.; Tang, X.; Zhang, M.; Li, X.; Jiang, H. Org. Lett. 2013, 15, 6254. doi: 10.1021/ol403105p
[18]	Zhu, Z.; Tang, X.; Li, J.; Li, X.; Wu, W.; Deng, G.; Jiang, H. Org. Lett. 2017, 19, 1370. doi: 10.1021/acs.orglett.7b00203
[19]	Qu, Z.; Zhang, F.; Deng, G.-J.; Huang, H. Org. Lett. 2019, 21, 8239. doi: 10.1021/acs.orglett.9b02978
[20]	Li, G.; He, R.; Liu, Q.; Wang, Z.; Liu, Y.; Wang, Q. J. Org. Chem. 2019, 84, 8646. doi: 10.1021/acs.joc.9b01158
[21]	Shi, S.; Xu, K.; Jiang, C.; Ding, Z. J. Org. Chem. 2018, 83, 14791. doi: 10.1021/acs.joc.8b02437
[22]	Angyal, A.; Demjen, A.; Wolfling, J.; Puskas, L. G.; Kanizsai, I. J. Org. Chem. 2020, 85, 3587. doi: 10.1021/acs.joc.9b03288 pmid: 32020808
[23]	Vuillermet, F.; Bourret, J.; Pelletier, G. J. Org. Chem. 2021, 86, 388. doi: 10.1021/acs.joc.0c02148 pmid: 33269922
[24]	Miao, C.; Hou, Q.; Wen, Y.; Han, F.; Li, Z.; Yang, L.; Xia, C.-G. ACS Sustainable Chem. Eng. 2019, 7, 12008.
[25]	Pan, Z.; Song, C.; Zhou, W.; Cui, D.-M.; Zhang, C. New J. Chem. 2020, 44, 6182. doi: 10.1039/C9NJ05794C
[26]	Adhikary, S.; Majumder, L.; Pakrashy, S.; Srinath, R.; Mukherjee, K.; Mandal, C.; Banerji, B. ACS Omega 2020, 5, 14394. doi: 10.1021/acsomega.0c00934 pmid: 32596577
[27]	Jayram, J.; Jeena, V. Green Chem. 2017, 19, 5841. doi: 10.1039/C7GC02484C
[28]	Jayram, J.; Jeena, V. RSC Adv. 2018, 8, 37557. doi: 10.1039/C8RA07238H
[29]	Huang, H.; Ji, X.; Wu, W.; Jiang, H. Adv. Synth. Catal. 2013, 355, 170. doi: 10.1002/adsc.201200582
[30]	Chen, X.; Wang, Z.; Huang, H.; Deng, G.-J. Adv. Synth. Catal. 2018, 360, 4017. doi: 10.1002/adsc.v360.20
[31]	Toledo, I.; Grigolo, T. A.; Bennett, J. M.; Elkins, J. M.; Pilli, R. A. J. Org. Chem. 2019, 84, 14187. doi: 10.1021/acs.joc.9b01844 pmid: 31460764
[32]	Geng, X.; Wang, C.; Huang, C.; Bao, Y.; Zhao, P.; Zhou, Y.; Wu, Y.-D.; Feng, L.-L.; Wu, A.-X. Org. Lett. 2020, 22, 140. doi: 10.1021/acs.orglett.9b04060
[33]	Zeng, L.; Li, J.; Gao, J.; Huang, X.; Wang, W.; Zheng, X.; Gu, L.; Li, G.; Zhang, S.; He, Y. Green Chem. 2020, 22, 3416. doi: 10.1039/D0GC00375A
[34]	Salfeena, C. T. F.; Jalaja, R.; Davis, R.; Suresh, E.; Somappa, S. B. ACS Omega 2018, 3, 8074. doi: 10.1021/acsomega.8b01017
[35]	Bhagat, S. B.; Telvekar, V. N. Tetrahedron Lett. 2017, 58, 3662. doi: 10.1016/j.tetlet.2017.08.017
[36]	Tan, J.; Ni, P.; Huang, H.; Deng, G.-J. Org. Biomol. Chem. 2018, 16, 4227. doi: 10.1039/C8OB00981C
[37]	Roslan, I. I.; Ng, K.-H.; Jaenicke, S.; Chuah, G.-K. Catal. Sci. Technol. 2019, 9, 1528. doi: 10.1039/C9CY00141G
[38]	Reddy, N. N. K.; Rao, S. N.; Ravi, C.; Adimurthy, S. ACS Omega 2017, 2, 5235. doi: 10.1021/acsomega.7b00969
[39]	Xiong, J.; Wei, X.; Liu, Z.-M.; Ding, M.-W. J. Org. Chem. 2017, 82, 13735. doi: 10.1021/acs.joc.7b02606 pmid: 29148765
[40]	Reddy, C. N.; Sathish, M.; Adhikary, S.; Nanubolu, J. B.; Alarifi, A.; Maurya, R. A.; Kamal, A. Org. Biomol. Chem. 2017, 15, 2730. doi: 10.1039/C7OB00299H
[41]	Necardo, C.; Alfano, A. I.; Grosso, E. D.; Pelliccia, S.; Galli, U.; Novellino, E.; Meneghetti, F.; Giustiniano, M.; Tron, G. C. J. Org. Chem. 2019, 84, 16299. doi: 10.1021/acs.joc.9b02546
[42]	Man, L.; Copley, R. C. B.; Handlon, A. Org. Biomol. Chem. 2019, 17, 6566. doi: 10.1039/C9OB01100E
[43]	Zhu, Z.; Lin, H.; Liang, B.; Huang, J.; Liang, W.; Chen, L.; Huang, Y.; Chen, X.; Li, Y. Chem. Commun. 2020, 56, 5621. doi: 10.1039/C9CC10042C
[44]	Motornov, V.; Markos, A.; Beier, P. Chem. Commun. 2018, 54, 3258. doi: 10.1039/C8CC01446A
[45]	Arepally, S.; Babu, V. N.; Bakthadoss, M.; Sharada, D. S. Org. Lett. 2017, 19, 5014. doi: 10.1021/acs.orglett.7b01840 pmid: 28901153
[46]	Zhao, Y.; Hu, Y.; Li, X.; Wan, B. Org. Biomol. Chem. 2017, 15, 3413. doi: 10.1039/C7OB00701A
[47]	Li, X.; Wang, T.; Lu, Y.-J.; Ji, S.; Huo, Y.; Liu, B. Org. Biomol. Chem. 2018, 16, 7143. doi: 10.1039/C8OB01532E
[48]	He, Q.-X.; Liang, Y.-F.; Xu, C.; Yao, X.-K.; Cao, H.; Yao, H.-G. ACS Comb. Sci. 2019, 21, 149. doi: 10.1021/acscombsci.8b00149
[49]	Tian, X.; Song, L.; Rudolph, M.; Wang, Q.; Song, X.; Rominger, F.; Hashmi, A. S. K. Org. Lett. 2019, 21, 1598. doi: 10.1021/acs.orglett.9b00140
[50]	Wang, Q.; Chen, X.; Wang, X.-G.; Liu, H.-C.; Liang, Y.-M. Org. Lett. 2019, 21, 9874. doi: 10.1021/acs.orglett.9b03782
[51]	Geng, X.; Liu, S.; Wang, W.; Qu, J.; Wang, B. J. Org. Chem. 2020, 85, 12635. doi: 10.1021/acs.joc.0c01806
[52]	Li, L.; Luo, Q.; Cui, H.; Li, R.; Zhang, J.; Peng, T. ChemCatChem 2018, 10, 1607. doi: 10.1002/cctc.v10.7
[53]	Senadi, G. C.; Kudale, V. S.; Wang, J.-J. Green Chem. 2019, 21, 979. doi: 10.1039/C8GC03839B
[54]	Das, S.; Mallick, S.; Sarkar, S. D. J. Org. Chem. 2019, 84, 12111. doi: 10.1021/acs.joc.9b02090
[55]	Raja, D.; Philips, A.; Palani, P.; Lin, W.-Y.; Devikala, S.; Senadi, G. C. J. Org. Chem. 2020, 85, 11531. doi: 10.1021/acs.joc.0c01053
[56]	Lin, M.; Wu, F.; Liu, T.-H.; Chen, Z.-T.; Xu, X.-Z.; Ke, F. Chin. J. Org. Chem. 2020, 40, 2563. (in Chinese) doi: 10.6023/cjoc202004016
	(林媚, 吴凡, 刘天惠, 陈志涛, 许秀枝, 柯方, 有机化学, 2020, 40, 2563.) doi: 10.6023/cjoc202004016
[57]	Zhao, H.-B.; Hou, Z.-W.; Liu, Z.-J.; Zhou, Z.-F.; Song, J.; Xu, H.-C. Angew. Chem., Int. Ed. 2017, 56, 587. doi: 10.1002/anie.201610715
[58]	Wang, J.; Zhang, F.-D.; Tang, D.; Wu, P.; Zhang, X.-G.; Chen, B.-H. RSC Adv. 2017, 7, 24594. doi: 10.1039/C7RA01966A
[59]	Li, M.; Li, W.; Lin, C.-D.; Wang, J.-H.; Wen, L.-R. J. Org. Chem. 2019, 84, 6904. doi: 10.1021/acs.joc.9b00659
[60]	Wang, C.; Jiang, H.; Chen, W.; Dong, J.; Chen, Z.; Cao, H. Org. Biomol. Chem. 2017, 15, 6463. doi: 10.1039/C7OB01242J
[61]	Wang, C.; Wang, E.; Chen, W.; Zhang, L.; Zhan, H.; Wu, Y.; Cao, H. J. Org. Chem. 2017, 82, 9144. doi: 10.1021/acs.joc.7b01781
[62]	Wang, C.; Lai, J.; Chen, C.; Li, X.; Cao, H. J. Org. Chem. 2017, 82, 13740. doi: 10.1021/acs.joc.7b02612
[63]	Wang, C.; Yu, Y.; Su, Z.; Li, X.; Cao, H. Org. Lett. 2019, 21, 4420. doi: 10.1021/acs.orglett.9b00969
[64]	Liu, W.; Zhang, Y.; He, J.; Yu, Y.; Yuan, J.; Ye, X.; Zhang, Z.; Xue, L.; Cao, H. J. Org. Chem. 2019, 84, 11348. doi: 10.1021/acs.joc.9b01818
[65]	Liu, W.; He, J.; Liu, X.; Yu, Y.; Pei, Y.; Zhu, B.; Cao, H. J. Org. Chem. 2020, 85, 14954. doi: 10.1021/acs.joc.0c01715
[66]	Mauro, G. D.; Maryasin, B.; Kaiser, D.; Shaaban, S.; Gonzalez, L.; Maulide, N. Org. Lett. 2017, 19, 3815. doi: 10.1021/acs.orglett.7b01678
[67]	Xie, J.; Huang, Y.; Song, H.; Liu, Y.; Wang, Q. Org. Lett. 2017, 19, 6056. doi: 10.1021/acs.orglett.7b02767
[68]	Ma, H.; Zhang, X.; Chen, L.; Yu, W. J. Org. Chem. 2017, 82, 11841. doi: 10.1021/acs.joc.7b01361
[69]	Xia, B.; Chen, W.; Zhao, Q.; Yu, W.; Chang, J. Org. Lett. 2019, 21, 2583. doi: 10.1021/acs.orglett.9b00541
[70]	Xu, K.; Yang, R.; Yang, S.; Jiang, C.; Ding, Z. Org. Biomol. Chem. 2019, 17, 8977. doi: 10.1039/C9OB01895F
[71]	Wang, W.; Zhang, S.; Shi, G.; Chen, Z. Org. Biomol. Chem. 2021, 19, 6682. doi: 10.1039/D1OB00942G
[72]	Yu, H.; Xiao, L.; Yang, X.; Shao, L. Chem. Commun. 2017, 53, 9745. doi: 10.1039/C7CC05315K
[73]	Das, U. K.; Shimon, L. J. W.; Milstein, D. Chem. Commun. 2017, 53, 13133. doi: 10.1039/C7CC08322J
[74]	Huang, X.; Cong, X.; Mi, P.; Bi, X. Chem. Commun. 2017, 53, 3858. doi: 10.1039/C7CC00772H
[75]	Yu, Y.; Zhang, Y.; Wang, Z.; Liang, Y.-X.; Zhao, Y.-L. Org. Chem. Front. 2019, 6, 3657. doi: 10.1039/C9QO00856J
[76]	Cai, J.; Bai, H.; Wang, Y.; Xu, X.; Xie, H.; Liu, J. Chem. Commun. 2019, 55, 3821. doi: 10.1039/C9CC01257E
[77]	Li, Q.-Q.; Ochiai, K.; Lee, C.-A.; Ito, S. Org. Lett. 2020, 22, 6132. doi: 10.1021/acs.orglett.0c02203
[78]	Wang, Y.; Zhou, Y.; Song, Q. Chem. Commun. 2020, 56, 6106. doi: 10.1039/D0CC01919D

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