Application of Photochemical/Electrochemical Synthesis in C—H Functionalization of Quinoxalin-2(1H)-one

doi:10.6023/cjoc202103032

Abstract

Quinoxalin-2(1H)-ones are a kind of important nitrogen-containing heterocyclic compounds, which have strong biological activity and chemical properties, and play an important role in synthesis chemistry, functional materials, drugs and so on. In recent years, the construction of 3-functionalized quinoxalin-2(1H)-one by C—H functionalization has attracted the attention of many scholars and made important progress. Among them, green chemistry oriented photocatalysis and electrochemical synthesis are becoming powerful tools for C—H functionalization of quinoxaline-2(1H)-one. In view of the great influence of photochemistry in synthetic chemistry, the research status of C—H functionalization of quinoxaline- 2(1H)-one in visible light catalysis and electrochemical synthesis is summarized, hoping to promote the further development of green synthesis strategy in the functionalization of nitrogen-containing heterocycles.

Key words: quinoxalin-2(1H)-one, visible-light, electrochemistry, C—H functionalization

Cite this article

Xiang Liu, Wen Li, Canzhan Zhuang, Hua Cao. Application of Photochemical/Electrochemical Synthesis in C—H Functionalization of Quinoxalin-2(1H)-one[J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3459-3481.

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Fig. & Tab. 46

Figure 1. Biologically active 3-substituted quinoxalin-2(1H)-ones

Scheme 1. Application of photochemical/electrochemical synthesis in C—H functionalization of quinoxalin-2(1H)-one

Figure 2. Structures of common photocatalysts

Scheme 2. Cross-coupling reaction of quinoxalin-2-(1H)-ones with simple ether induced by visible light catalysis

Scheme 3. Cyanoalkylation of quinoxalin-2(1H)-ones induced by visible light catalysis

Scheme 4. Cyanoalkylation of quinoxalin-2(1H)-ones induced by visible light catalysis

Scheme 5. Visible-light-induced cyanoalkylation of quinoxalin-2(1H)-ones

Scheme 6. Regioselective alkylation of quinoxalin-2-(1H)-ones under visible light catalysis

Scheme 7. Visible light-induced regioselective decarboxylative alkylation of quinoxalin-2(1H)-ones

Scheme 8. Visible light-induced regioselective decarboxylative alkylation of quinoxalin-2(1H)-ones

Scheme 9. Visible-light induced decarboxylative alkylation of quinoxalin-2(1H)-ones

Scheme 10. Visible-light-induced alkylation of quinoxalin- 2(1H)-ones

Scheme 11. Cross dehydrogenative coupling reaction between quinoxalin-2(1H)-ones and ethers induced by visible light

Scheme 12. Perfluoroalkylation of quinoxalin-2(1H)-ones induced by visible light

Scheme 13. Photoinitiated three-component α-perfluoroalkyl-β- heteroarylation of unactivated alkenes via electron catalysis

Scheme 14. Visible-light-induced self-catalyzed trifluoromethylation of quinoxalin-2(1H)-ones under photocatalyst free conditions

Scheme 15. Visible-light photoredox and organoamine catalysis for the C-3 difluoroalkylation of quinoxalin-2(1H)-ones

Scheme 16. BI-OAc-accelerated C(3)—H alkylation of quinoxalin-2(1H)-ones under visible-light irradiation

Scheme 17. Direct C—H difluoromethylation of quinoxalin-2(1H)-ones via organic photoredox catalysis

Scheme 18. Photoinitiated decarboxylative C(3)-difluoro- arylmethylation of quinoxalin-2(1H)-ones with potassium 2,2-difluoro-2-arylacetates

Scheme 19. Visible-light-induced 3-arylation of quinoxalin- 2(1H)-ones with aryl diazonium salts

Scheme 20. Visible light photoredox-catalyzed arylation of quinoxalin-2(1H)-ones with aryldiazonium salts

Scheme 21. Visible-light-promoted acridine red catalyzed aerobic oxidative decarboxylative acylation of α-oxo-carboxylic acids with quinoxalin-2(1H)-ones

Scheme 22. Visible-light-induced decarboxylative acylation of quinoxalin-2(1H)-ones with α-oxo carboxylic acids

Scheme 23. Acylation of quinoxalin-2(1H)-ones under visible light catalysis

Scheme 24. Visible-light-induced decarboxylation of quinoxalin-2(1H)-ones with aryl peroxide

Scheme 25. Cross-dehydrogenative coupling of quinoxalin-2(1H)-ones with aliphatic amines under visible-light catalysis

Scheme 26. Visible-light-initiated cross-dehydrogenative coupling of quinoxalin-2(1H)-ones and simple amides

Scheme 27. Visible-light photoredox catalyzed C—N coupling of quinoxaline-2(1H)-ones with azoles without external photosensitizer

Scheme 28. Visible-light-induced alkoxylation of quinoxalin-2(1H)-ones with alcohols

Scheme 29. (Thio)etherification of quinoxalinones under visible-light photoredox catalysis

Scheme 30. Visible-light-induced fluoroalkoxylation of quinoxalin-2(1H)-ones with fluoroalkyl alcohols

Scheme 31. Cross-dehydrogenative coupling of quinoxalin- 2(1H)-ones with alcohols under visible-light catalysis

Scheme 32. Direct C—H sulfenylation of quinoxalin-2(1H)- ones with thiols under visible-light-induced photocatalyst-free conditions

Scheme 33. Visible-light-promoted direct C—H/S—H cross- coupling of quinoxalin-2(1H)-ones with thiols

Scheme 34. Visible light photoredox-catalyzed phosphorylation of quinoxalin-2(1H)-ones

Scheme 35. Silylation of quinoxalin-2(1H)-ones under visible light catalysis

Scheme 36. Trifluoromethylation of quinoxalin-2(1H)-ones under electrochemical conditions

Scheme 37. Electrochemical decarboxylative C-3 alkylation of quinoxalin-2(1H)-ones with N-hydroxyphthalimide esters

Scheme 38. Deoxyalkylation of quinoxalin-2(1H)-ones under electrochemical conditions

Scheme 39. Electrochemical C-3 pyridination of quinoxalin- 2(1H)-ones

Scheme 40. Electro-oxidative C—H alkylation of quinoxalin-2(1H)-ones with organoboron compounds

Scheme 41. Electrochemical dehydrogenative cross-coupling of quinoxalin-2(1H)-ones with amines

Scheme 42. Electrochemical C-3 alkoxylation of quinoxalin-2(1H)-ones

Scheme 43. Electrochemically oxidative cross-coupling between quinoxalin-2(1H)-ones and thiols

Scheme 44. Electrochemical phosphorylation of quinoxalin-2 (1H)-ones

References 52

[1]	Yang, Y. C.; Zhang, S. Z.; Wu, B. B.; Ma, M. M.; Chen, X.; Qin, X. Y.; He, M. L.; Hussain, S.; Jing, C. J.; Ma, B.; Zhu, C. ChemMedChem 2012, 7, 823. doi: 10.1002/cmdc.v7.5 pmid: 24793885
	(b) Shi, L. L.; Hu, W.; Wu, J. F.; Zhou, H. Y.; Zhou, H.; Li, L. Mini-Rev. Med. Chem. 2018, 18, 392. doi: 10.2174/1389557517666171101111134 pmid: 24793885
	(c) Hussain, S.; Parveen, S.; Hao, X.; Zhang, S. Z.; Wang, W.; Qin, X. Y.; Yang, Y. C.; Chen, X.; Zhu, S. J.; Zhu, C. J.; Ma, B. Eur. J. Med. Chem. 2014, 80, 383. doi: 10.1016/j.ejmech.2014.04.047 pmid: 24793885
	(d) Shi, J. W.; Wei, W. Chin. J. Org. Chem. 2020, 40, 2170. (in Chinese). doi: 10.6023/cjoc202000041 pmid: 24793885
	( 时建伟, 魏伟, 有机化学, 2020, 40, 2170.) pmid: 24793885
	(e) Mao, P.; Zhu, J. L.; Yuan, J. W.; Liang, L. R.; Xiao, Y. M.; Zhang, C. S. Chin. J. Org. Chem. 2019, 39, 1529. (in Chinese). doi: 10.6023/cjoc201904025 pmid: 24793885
	( 毛璞, 朱军亮, 袁金伟, 杨亮茹, 肖咏梅, 张长森, 有机化学, 2019, 39, 1529.) pmid: 24793885
	(f) Hai, M.; Guo, L. N.; Wang, L.; Duan, X. H. Acta. Chim. Sinica 2019, 77, 895. (in Chinese). doi: 10.6023/A19040155 pmid: 24793885
	( 海曼, 郭丽娜, 王乐, 段新华, 化学学报, 2019, 77, 895.) pmid: 24793885
[2]	(a) Weïwer, M.; Spoonamore, J.; Wei, J.; Guichard, B.; Ross, N. T.; Masson, K.; Silkworth, W.; Dandapani, S.; Palmer, M.; Scherer, C. A.; Stern, A. M.; Schreiber, S. L.; Munoz, B. ACS Med. Chem. Lett. 2012, 3, 1034. doi: 10.1021/ml300246r pmid: 11170649
	(b) Qin, X. Y.; Hao, X.; Han, H.; Zhu, S. J.; Yang, Y. C.; Wu, B. B.; Hussain, S.; Parveen, S.; Jing, C. J.; Ma, B.; Zhu, C. J. J. Med. Chem. 2015, 58, 1254. doi: 10.1021/jm501484b pmid: 11170649
	(c) Ajani, O. O. Eur. J. Med. Chem. 2014, 85, 688. doi: 10.1016/j.ejmech.2014.08.034 pmid: 11170649
	(d) Lawrence, D. S.; Copper, J. E.; Smith, C. D. J. Med. Chem. 2001, 44, 594. pmid: 11170649
	(e) Liu, Z.; Yu, S.; Chen, D.; Shen, G.; Wang, Y.; Hou, L.; Lin, D.; Zhang, J.; Ye, F. Drug Des., Dev. Ther. 2016, 10, 1489. pmid: 11170649
[3]	(a) Qin, Y.; Zhu, L.; Luo, S. Chem. Rev. 2017, 117, 9433. doi: 10.1021/acs.chemrev.6b00657
	(b) Ping, L.; Chung, D. S.; Bouffard, J.; Lee, S. G. Chem. Soc. Rev. 2017, 46, 4299. doi: 10.1039/C7CS00064B
	(c) Shen, J. B.; Xu, J.; Huang, L.; Zhu, Q.; Zhang, P. F. Adv. Synth. Catal. 2020, 362, 230. doi: 10.1002/adsc.v362.1
	(d) Yuan, J. W.; Liu, S. N.; Qiao, L. B. Adv. Synth. Catal. 2017, 359, 4197. doi: 10.1002/adsc.v359.23
	(e) Ramesh, B.; Reddy, C. R.; Kumar, G. R.; Reddy, B. V. S. Tetrahedron Lett. 2018, 59, 628. doi: 10.1016/j.tetlet.2017.12.085
	(f) Aganda, K. C. C.; Hong, B.; Lee, A. Adv. Synth. Catal. 2021, 363, 1443. doi: 10.1002/adsc.v363.5
[4]	(a) Yuan, J. W.; Fu, J. H.; Yin, J. H.; Dong, Z. H.; Xiao, Y. M.; Mao, P.; Qu, L. B. Org. Chem. Front. 2018, 5, 2820. doi: 10.1039/C8QO00731D
	(b) Wang, L. P.; Zhang, Y. C.; Li, F. F.; Hao, X. Y.; Zhang, H. Y.; Zhao, J. Q. Adv. Synth. Catal. 2018, 360, 3969. doi: 10.1002/adsc.v360.20
	(c) Hong, G. F.; Yuan, J. W.; Fu, J. H.; Pan, G. Y.; Wang, Z. W.; Yang, L. R.; Xiao, Y. M.; Mao, P.; Zhang, X. M. Org. Chem. Front. 2019, 6, 1173. doi: 10.1039/C9QO00105K
	(d) Wang, J.; Li, J.; Wei, Y. Y.; Yang, J. Y.; Huo, C. D. Org. Chem. Front. 2018, 5, 3534. doi: 10.1039/C8QO01049H
	(e) Ke, Q. M.; Yan, G. B.; Yu, J.; Wu, X. M. Org. Biomol. Chem. 2019, 17, 5863. doi: 10.1039/C9OB00782B
[5]	(a) He, K. H.; Tan, F. F.; Zhou, C. Z.; Zhou, G. J.; Yang, X. L.; Li, Y. Angew. Chem., nt. Ed. 2017, 56, 3080.
	(b) Wang, H. M.; Gao, X. L.; Lv, Z. C.; Abdelilah, T.; Lei, A. W. Chem. Rev. 2019, 119, 6769. doi: 10.1021/acs.chemrev.9b00045
	(c) Yu, X. Y.; Chen, J. R.; Xiao, W. J. Chem. Rev. 2021, 121, 506. doi: 10.1021/acs.chemrev.0c00030
	(d) Mcatee, R. C.; Mcclain, E. J.; Stephenson, C. R. J. Trends Chem. 2019, 1, 111. doi: 10.1016/j.trechm.2019.01.008
	(d) Bhaskaran, R. P.; Babu, B. P. Adv. Synth. Catal. 2020, 362, 5219. doi: 10.1002/adsc.v362.23
	(e) Pan, X. L.; Xia, H. G.; Wu, J. Org. Chem. Front. 2016, 3, 1163.
	(f) Shen, J. B.; Xu, J.; He, L.; Ouyang, Y.; Haung, L.; Li, W. M.; Zhu, Q.; Zhang, P. F. Org. Lett. 2021, 23, 1204. doi: 10.1021/acs.orglett.0c04148
	(g) Xu, J.; Huang, L.; He, L.; Ni, Z. G.; Shen, J. B.; Li, X. L.; Chen, K. X.; Li, W. M.; Zhang, P. F. Green Chem. 2021, 23, 2123. doi: 10.1039/D0GC04235H
[6]	(a) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 7, 5322.
	(b) Romero, N. A.; Nicewicz, D. A. Chem. Rev. 2016, 17, 10075.
	(c) Hari, D. P.; König, B. Chem. Commun. 2014, 50, 6688. doi: 10.1039/C4CC00751D
[7]	(a) Jiang, Y. Y.; Xu, K.; Zeng, C. C. Chem. Rev. 2018, 9, 4485.
	(b) Waldvogel, S. R.; Lips, S.; Selt, M.; Riehl, B.; Kampf, C. J. Chem. Rev. 2018, 118, 6706. doi: 10.1021/acs.chemrev.8b00233
	(c) Pegis, M. L.; Wise, C. F.; Martin, D. J.; Mayer, J. M. Chem. Rev. 2018, 5, 2340.
	(d) Wang, H. Q.; Xu, W. T.; Xin, L. L.; Liu, W. M.; Wang, Z. Q.; Xu, K. J. Org. Chem. 2016, 81, 3681. doi: 10.1021/acs.joc.6b00343
[8]	(a) Cui, Z. M.; Zhu, B. F.; Li, X. C.; Cao, H. Org. Chem. Front. 2018, 5, 2219. doi: 10.1039/C8QO00443A
	(b) Yu, Y.; Su, Z. Q.; Cao, H. Chem. Rec. 2019, 19, 2105. doi: 10.1002/tcr.v19.10
	(c) Cao, H.; Lei, S.; Li, N. Y.; Chen, L. B.; Liu, J. Y.; Cai, H. Y.; Qiu, S. X.; Tan, J. W. Chem. Commun. 2015, 51, 1823 doi: 10.1039/C4CC09134E
	(d) Lei, S.; Cao, H.; Chen, L. B.; Liu, J. Y.; Cai, H. Y. Adv. Synth. Catal. 2015, 357, 3109. doi: 10.1002/adsc.201500391
[9]	(a) Brahmachari, G. RSC Adv. 2016, 6, 64676. doi: 10.1039/C6RA14399G
	(b) Resch, V.; Schrittwieser, J. H.; Siirola, E.; Kroutil, W. Curr. Opin. Biotechnol. 2011, 22, 793. doi: 10.1016/j.copbio.2011.02.002
	(c) Yamaguchi, J.; Yamaguchi, A. D.; Itami, K. Angew. Chem., Int. Ed. 2012, 51, 8960. doi: 10.1002/anie.201201666
[10]	Wei, W.; Wang, L. L.; Yue, H. L.; Bao, P. L.; Liu, W. W.; Hu, C. S.; Yang, D. S.; Wang, H. ACS Sustainable Chem. Eng. 2018, 6, 17252. doi: 10.1021/acssuschemeng.8b04652
[11]	Zhang, W.; Pan, Y. L.; Yang, C.; Chen, L.; Li, X.; Cheng, J. P. J. Org. Chem. 2019, 84, 7786. doi: 10.1021/acs.joc.9b00657 pmid: 31140803
[12]	Zhang, W.; Pan, Y. L.; Yang, C.; Li, X.; Wang, B. Org. Chem. Front. 2019, 6, 2765. doi: 10.1039/c9qo00625g
[13]	Zhao, B.; Kong, X. Q.; Xu, B. Tetrahedron Lett. 2019, 60, 2063. doi: 10.1016/j.tetlet.2019.06.059
[14]	Zhang, H. D.; Xu, J.; Zhao, J. M.; Zhang, P. F.; Li, W. M. Org. Biomol. Chem. 2019, 17, 10201. doi: 10.1039/C9OB02203A
[15]	Liu, L. X.; Pan, N.; Sheng, W.; Su, L. B.; Liu, L.; Dong, J. Y.; Zhou, Y. B.; Yin, S. F. Adv. Synth. Catal. 2019, 361, 4126. doi: 10.1002/adsc.v361.17
[16]	Yan, Z. Y.; Sun, B.; Zhang, X.; Zhuang, X. H.; Yang, J.; Su, W. K.; Jin, C. Chem.-Asian J. 2019, 14, 3344. doi: 10.1002/asia.v14.19
[17]	Xue, W. X.; Su, Y. P.; Wang, K. H.; Zhang, R.; Feng, Y. W.; Cao, L. D.; Huang, D. F.; Hu, Y. L. Org. Biomol. Chem. 2019, 17, 6654. doi: 10.1039/C9OB01169B
[18]	Xie, L. Y.; Jiang, L. L.; Tan, J. X.; Wang, Y.; Xu, X. Q.; Zhang, B.; Cao, Z.; He, W. M. ACS Sustainable Chem. Eng. 2019, 7, 14153. doi: 10.1021/acssuschemeng.9b02822
[19]	Mane, K. D.; Kamble, R. B.; Suryavanshi, G. New J. Chem. 2019, 43, 7403. doi: 10.1039/C9NJ00075E
[20]	Wei, Z. J.; Qi, S. J.; Xu, Y. H.; Liu, H.; Wu, J. Z.; Li, H. S.; Xia, C. C.; Duan, G. Y. Adv. Synth. Catal. 2019, 361, 5490. doi: 10.1002/adsc.v361.23
[21]	Zheng, D. Q.; Studer, A. Org. Lett. 2019, 21, 325. doi: 10.1021/acs.orglett.8b03849
[22]	Wang, J. Y.; Sun, B.; Zhang, L.; Xu, T. W.; Xie, Y. Y.; Jin, C. Asian J. Org. Chem. 2019, 8, 1942. doi: 10.1002/ajoc.v8.10
[23]	Jin, C.; Zhuang, X. C.; Sun, B.; Li, D. Y.; Zhu, R. Asian J. Org. Chem. 2019, 8, 1490. doi: 10.1002/ajoc.v8.8
[24]	He, X. K.; Lu, J.; Zhang, A. J.; Zhang, Q. Q.; Xu, G. Y.; Xuan, J. Org. Lett. 2020, 22, 5984. doi: 10.1021/acs.orglett.0c02080
[25]	Zhang, W.; Xiang, X. X.; Chen, J. Y.; Yang, C.; Pan, Y. L.; Cheng, J. P.; Meng, J. B.; Li, X. Nat. Commun. 2020, 11, 638. doi: 10.1038/s41467-020-14494-8 pmid: 32005825
[26]	Gao, Y. H.; Zhao, L. L.; Xiang, T. Y.; Li, P. H.; Wang, L. RSC Adv. 2020, 10, 10559. doi: 10.1039/D0RA02059A
[27]	Wang, L. L.; Bao, P. L.; Liu, W. W.; Liu, S. T.; Hu, C. S.; Yue, H. L.; Yang, D. S.; Wei, W. Chin. J. Org. Chem. 2018, 38, 3189. (in Chinese). doi: 10.6023/cjoc201807014
	( 王雷雷, 鲍鹏丽, 刘维伟, 刘思彤, 胡昌松, 岳会兰, 杨道山, 魏伟, 有机化学, 2018, 38, 3189.)
[28]	Kwon, S. J.; Jung, H. I.; Kim, D. Y. ChemistrySelect 2018, 3, 5824. doi: 10.1002/slct.v3.21
[29]	Bao, P. L.; Liu, F.; Lv, Y. F.; Yue, H. L.; Li, J. S.; Wei, W. Org. Chem. Front. 2019, 2020, 492.
[30]	Xie, L. Y.; Bai, Y. S.; Xu, X. Q.; Xia, P.; Tang, H. S.; Huang, Y.; Lin, Y. W.; Cao, Z.; He, W. M. Green Chem. 2020, 22, 1720. doi: 10.1039/C9GC03899J
[31]	Lu, J.; He, X. K.; Cheng, X.; Zhang, A.; Xu, G. Y.; Xuan, J. Adv. Synth. Catal. 2020, 362, 2179.
[32]	Xie, L.Y.; Peng, S.; Peng, L. H.; Peng, C.; Lin, Y. W.; Yu, X. Y.; Cao, Z.; Peng, Y. Y.; He, W. M. Green Chem. 2021, 23, 374. doi: 10.1039/D0GC02844D
[33]	Wei, W.; Wang, L. L.; Bao, P. L.; Shao, Y.; Yue, H. L.; Yang, D. S.; Yang, X. B.; Zhao, X. H.; Wang, H. Org. Lett. 2018, 20, 7125. doi: 10.1021/acs.orglett.8b03079 pmid: 30372088
[34]	Xie, L. Y.; Hu, J. L.; Song, Y. X.; Jia, G. K.; Lin, Y. W.; He, J. Y.; Cao, Z.; He, W. M. ACS Sustainable Chem. Eng. 2019, 7, 19993. doi: 10.1021/acssuschemeng.9b05715
[35]	Sun, M. L.; Wang, L.; Zhao, L. L.; Wang, Z. M.; Li, P. H. ChemCatChem 2020, 12, 5261. doi: 10.1002/cctc.v12.20
[36]	Zhao, L. L.; Wang, L.; Gao, Y. H.; Wang, Z. M.; Li, P. H. Adv. Synth. Catal. 2019, 361, 1. doi: 10.1002/adsc.v361.1
[37]	Zhou, J. D.; Zhou, P.; Zhao, T. T.; Ren, Q. L.; Li, J. J. Adv. Synth. Catal. 2019, 361, 5371. doi: 10.1002/adsc.v361.23
[38]	Xu, X. B.; Xia, C. C.; Li, X. J.; Sun, J.; Hao, L. Q. RSC Adv. 2020, 10, 2016. doi: 10.1039/C9RA10194B
[39]	Xie, L. Y.; Liu, Y. S.; Ding, H. R.; Gong, S.; Tan, J. X.; He, J. Y.; Gao, Z.; He, W. M. Chin. J. Catal. 2020, 41, 1168. doi: 10.1016/S1872-2067(19)63526-6
[40]	Teng, Q. H.; Yao, Y.; Wei, W. X.; Tang, H. T.; Li, J. R.; Pan, Y. M. Green Chem. 2019, 21, 6241. doi: 10.1039/C9GC03045J
[41]	Xie, L. Y.; Chen, Y. L.; Qin, L.; Wen, Y.; Xie, J. W.; Tan, J. X.; Huang, Y.; Cao, Z.; He, W. M. Org. Chem. Front. 2019, 6, 3950. doi: 10.1039/C9QO01240K
[42]	Kim, Y.; Kim, D. Y. Tetrahedron Lett. 2018, 59, 2443. doi: 10.1016/j.tetlet.2018.05.034
[43]	Dai, C. H.; Zhan, Y. L.; Liu, P.; Sun, P. P. Green Chem. 2021, 23, 314. doi: 10.1039/D0GC03697H
[44]	Dou, G. Y.; Jiang, Y. Y.; Xu, K.; Zeng, C. C. Org. Chem. Front. 2019, 6, 2392. doi: 10.1039/C9QO00552H
[45]	Niu, K. K.; Song, L. Y.; Hao, Y. K.; Wang, Q. M. Chem. Commun. 2020, 56, 11673. doi: 10.1039/D0CC05391K
[46]	Gao, Y. Y.; Wu, Z. G.; Yu, L.; Wang, Y.; Pan, Y. Angew. Chem., Int. Ed. 2020, 59, 10859. doi: 10.1002/anie.v59.27
[47]	Wen, J. W.; Yang, X. T.; Yan, K. L.; Qin, H. Y.; Ma, J.; Sun, X. J.; Yang, J. J.; Wang, H. Org. Lett. 2021, 23, 1081. doi: 10.1021/acs.orglett.0c04296
[48]	Niu, K. K.; Hao, Y. K.; Song, L. Y.; Liu, Y. X.; Wang, Q. M. Green Chem. 2021, 23, 302. doi: 10.1039/D0GC03892J
[49]	Li, K. J.; Xu, K.; Liu, Y. G.; Zeng, C. C.; Sun, B. G. Adv. Synth. Catal. 2018, 361, 1033. doi: 10.1002/adsc.v361.5
[50]	Jiang, X. P.; Yang, L. C.; Ye, Z. H.; Du, X. F.; Fang, L. Y.; Zhu, Y.; Chen, K. D.; Li, J. J.; Yu, C. M. Eur. J. Org. Chem. 2020, 2020, 1687.
[51]	Zhou, J. D.; Li, Z. H.; Sun, Z. X.; Ren, Q. L.; Zhang, Q. W.; Li, H.; Li, J. J. J. Org. Chem. 2020, 85, 4365. doi: 10.1021/acs.joc.0c00050
[52]	Li, K. J.; Jiang, Y. Y.; Xu, K.; Zeng, C. C.; Sun, B. G. Green Chem. 2019, 21, 4412. doi: 10.1039/C9GC01474H

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