Recent Advances in the Electrochemical Formation of Carbon-Nitrogen Bonds

doi:10.6023/cjoc202012013

Abstract

C—N bonds are widely existed in drugs, natural products, and functional materials. Thus, the construction of C—N bonds is one of the most important research areas in academia and industry. Recently, the renaissance in organic electrochemistry has promoted the electrochemical C—N bond formations to be a special branch of organic synthesis. The most recent advances in the electrochemical C—N bond formations since 2015 are summarized. The reaction mechanisms of these transformations are discussed, and the challenges and future directions of this important filed are included. We hope that this review can give references to the researchers, graduate students and other related people.

Key words: organic electrochemistry, carbon-nitrogen bond, green chemistry

Cite this article

Zeyin Meng, Chengtao Feng, Kun Xu. Recent Advances in the Electrochemical Formation of Carbon-Nitrogen Bonds[J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2535-2570.

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Fig. & Tab. 67

Scheme 1. Electrochemically oxidative intramolecular cyclization of 2'-amino-acetophenones

Scheme 2. Electrochemical benzylic C(sp3)—H amination

Scheme 3. Electrochemically induced oxidative intramolecular C(sp3)—H amination

Scheme 4. Electrochemical synthesis of trans-2,3-disubstituted aziridines

Scheme 5. Electrochemical synthesis of β-enaminones

Scheme 6. Electrochemical synthesis of α-enaminones

Scheme 7. Electro-oxidative C(sp3)—H amination with azoles

Scheme 8. Electrochemical oxidative azolation of lactams

Scheme 9. Electrochemically intermolecular C(sp3)—H/N—H cross-coupling of xanthenes with N-alkoxyamide

Scheme 10. Electrochemical intermolecular C(sp3)—H/N—H coupling of methyl N?heteroaromatics with amines

Scheme 11. Electrochemical synthesis of gem-diamines

Scheme 12. Electrooxidative annulation of N-allyl amides with 1,3-dicarbonyl compounds

Scheme 13. Electrochemically induced cyclic ketones α-C—H aminations

Scheme 14. Electrooxidation induced [4+2] annulation for the synthesis of pyrazines

Scheme 15. Electrochemically initiated intermolecular cyclization of ketones with 2-aminopyridines

Scheme 16. Electrochemical synthesis of allylamines

Scheme 17. Electrochemical benzylic C—H amination reaction

Scheme 18. Site-selective electrochemical benzylic C—H amination reaction

Scheme 19. Manganese-catalyzed electrophotochemical azidation of C(sp3)—H bonds

Scheme 20. Electrooxidation induced intramolecular olefin hydroamidation reaction

Scheme 21. Electrochemical oxidative intramolecular amination of multisubstituted alkenes

Scheme 22. Electrochemical synthesis of (aza)indolines via dehydrogenative [3+2] annulation

Scheme 23. Electrochemical synthesis of 7-membered carbocycles via tandem radical cyclization

Scheme 24. Amidinyl radical formation via anodic oxidation and its application in aromatic C—H bond functionalization

Scheme 25. Cathode material determined product selectivity for electrochemical C—H functionalization of biaryl ketoximes

Scheme 26. Regioselective intramolecular amidation of C(sp2/sp3)—H bonds

Scheme 27. Nitrogen-centered radical induced aryl migration reaction

Scheme 28. Electrochemical induced intramolecular C—H amination

Scheme 29. Regioselective synthesis of N-heteroaromatics from biaryl aldehydes and NH3

Scheme 30. Iodide-mediated electrosynthesis of indolines and indoles

Scheme 31. Electrochemical synthesis of 3-azido-indolines

Scheme 32. Electrochemical aziridination of alkenes

Scheme 33. Electrooxidative C—H amination of quinoxalin- 2(1H)-ones

Scheme 34. Electrooxidation induced intermolecular aromatic C—H imidation

Scheme 35. Electrooxidation induced [3+2] annulation for the preparation of indolines

Scheme 36. Electrochemical synthesis of 1,2,4-triazole-fused heterocycles

Scheme 37. Electrochemical oxidative C—H amination of phenols

Scheme 38. Electrochemical oxidation induced selective modification of biomolecules with tyrosine

Scheme 39. Electrochemical synthesis of oxazinones

Scheme 40. Electrochemically enabled chemoselective sulfonylation and hydrazination of indoles

Scheme 41. Electrochemical ortho-selective amination of aromatic ethers

Scheme 42. Electrochemical C—N bond formation through C—C bond cleavage

Scheme 43. Electrochemical aziridination of triaryl ethylenes

Scheme 44. 1,2-Diamination of alkenes via activation of alkenes

Scheme 45. Electrochemical intermolecular oxidative C—H/ N—H cross-coupling reaction

Scheme 46. Electrochemical intramolecular oxidative C—H/ N—H cross-couplings

Scheme 47. Electrochemical amination of aromatic amines with high para-selectivity

Scheme 48. Metal-catalyzed electrochemical alkene diazidation

Scheme 49. Cobalt(II)-catalyzed electrooxidative C—H amination of arenes

Scheme 50. Nickel-catalyzed electrooxidative C—H amination of arenes

Scheme 51. Cobalt-catalyzed electrochemical C—H amination

Scheme 52. Synergistic combination of copper catalysis and electrooxidation for C(sp2)—H amination

Scheme 53. Copper-catalyzed electrochemical C—H amination of arenes with secondary amines

Scheme 54. Electrochemical synthesis of highly functionalized (aza)indoles

Scheme 55. Electrolytic cyclization leading to N-doped polycyclic aromatic hydrocarbons

Scheme 56. Electrochemical synthesis of imidazo-fused N- heteroaromatic compounds

Scheme 57. Electrosynthesis of benzimidazolones and benzoxazolones

Scheme 58. Electrochemical C—H/N—H activation by cobalt catalysis

Scheme 59. Cobalt-catalyzed electrooxidative C—H activation for the allene annulations

Scheme 60. Electrochemically cobalt-catalyzed [4+2] annulations of internal alkynes

Scheme 61. Cobalt-catalyzed electrooxidative C—H annulation with 1,3-diynes

Scheme 62. Rh-catalyzed C—H annulation under electroflow conditions

Scheme 63. Rh-catalyzed electrochemical synthesis of aza- nanographene

Scheme 64. Ruthenium-catalyzed electrochemical dehydrogenative annulation of anilines with alkynes

Scheme 65. Electrochemically dehydrogenative annulation of amides with alkynes

Scheme 66. Cobalt-catalyzed electrochemical [4+2] annulation reaction

Scheme 67. Electrochemical oxidative aminocarbonylation of terminal alkynes

References 79

[1]	Pozharskiĭ,A. F.; Katritzky,A. R., Heterocycles in Life and Society: An Introduction to Heterocyclic Chemistry, Biochemistry and Applications, 2nd ed., Wiley, United Kingdom, 2011.
[2]	Novel Drug Approvals for 2019. Retrieved December 15, 2019, from https://www.fda.gov/drugs/newdrugs-fda-cders-new-molecu-lar-entities-and-new-therapeutic-biological-products/novel-drug-approvals-2019
[3]	Wermuth, C. The Practice of Medicinal Chemistry, Academic Press, USA, 2003.
[4]	Hao, Z.; Iqbal, A. Chem. Soc. Rev. 1997,26, p. 203.
[5]	(a) Hartwig,J. F. Handbook of Organopalladium Chemistry for Organic Synthesis, John Wiley & Sons Inc., USA, 2002,1051.
	(b) Sambiagio, C.; Marsden,S. P.; Blacker,A. J.; McGowan,P. C. Chem. Soc. Rev. 2014, 43,3525. doi: 10.1039/C3CS60289C
	(c) Ruiz-Castillo, P.; Buchwald,S. L. Chem. Rev. 2016, 116,12564. doi: 10.1021/acs.chemrev.6b00512
	(d) 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.)
[6]	(a) Zhao, J.; Zhang, Q. Acta Chim. Sinica 2015, 73,1235 (in Chinese). doi: 10.6023/A15010063
	( 赵金钵, 张前, 王佳, 化学学报. 2015, 73,1235.)
	(b) Europe, P. Chem. Rev. 2016, 116,12564. doi: 10.1021/acs.chemrev.6b00512
	(c) Baeten, M.; Maes,B. U.W. Adv. Organomet. Chem. 2017, 67,401. doi: 10.1016/S0022-328X(00)88186-3
	(d) Luo, J.; Wei,W. T. Adv. Synth. Catal. 2018, 360,2076. doi: 10.1002/adsc.v360.11
	(e) Wang, P.; Deng, L. Chin. J. Chem. 2018, 36,1222. doi: 10.1002/cjoc.v36.12
	(f) Liu, Q.; Lv, Y.; Bao, P.; Yue, H.; Wei, W. Chin. J. Org. Chem. 2020, 40,4015 (in Chinese). doi: 10.6023/cjoc202008042
	( 刘启顺, 吕玉芬, 鲍鹏丽, 岳会兰, 魏伟, 有机化学. 2020, 40,4015.)
	(g) Hua, B.; Yang, Q.; Xiao, W. Chin. J. Org. Chem. 2020, 40,3559 (in Chinese). doi: 10.6023/cjoc202006072
	( 华庭碧, 阳青青, 肖文精, 有机化学. 2020, 40,3559.)
	(h) Dong, K.; Liu, Q.; Wu,L. -Z. Acta Chim. Sinica 2020, 78,299 (in Chinese). doi: 10.6023/A19110412
	( 董奎, 刘强, 吴骊珠, 化学学报. 2020, 78,299.)
[7]	McElroy,C. R.; Constantinou, A.; Jones,L. C.; Summerton, L.; Clark,J. H. Green Chem. 2015, 17,3111. doi: 10.1039/C5GC00340G
[8]	Francke, R.; Little,R. D. Chem. Soc. Rev. 2014, 43,2492. doi: 10.1039/c3cs60464k
[9]	(a) A. G.; McElroy, A.; Maruyama,C. R.; Inokuma, Y.; Fujita, M.; Baran,P. S.; Blackmond,D. G.. Angew. Chem.,Int. Ed. 2014, 53,11868. doi: 10.1002/anie.201407948
	(b) Horn,E. J.; Rosen,B. R.; Baran,P. S. ACS Cent. Sci. 2016, 2,302. doi: 10.1021/acscentsci.6b00091
	(c) Dou,G. Y.; Jiang,Y. Y.; Xu, K.; Zeng,C. C. Org. Chem. Front. 2019, 6,2392. doi: 10.1039/C9QO00552H
	(d) Jiang, Y.; Xu, K.; Zeng,C. C. CCS Chem. 2021, 3,1911.
[10]	(a) Yang,Q. -L.; Fang, P.; Mei,T. -S. Chin. J. Chem. 2018, 36,338. doi: 10.1002/cjoc.v36.4
	(b) Yuan, Y.; Lei,A. W. Acc. Chem. Res. 2019, 52,3309. doi: 10.1021/acs.accounts.9b00512
	(c) Ackermann, L. Acc. Chem. Res. 2020, 53,84. doi: 10.1021/acs.accounts.9b00510
	(d) Jiao,K. -J.; Xing,Y. -K.; Yang,Q. -L.; Qiu, H.; Mei,T. -S. Acc. Chem. Res. 2020, 53,300. doi: 10.1021/acs.accounts.9b00603
[11]	(a) Jiang,Y. Y.; Xu, K.; Zeng,C. C. Chem. Rev. 2018, 118,4485. doi: 10.1021/acs.chemrev.7b00271
	(b) Ye, Z.; Zhang, F. Chin. J. Org. Chem. 2020, 40,241 (in Chinese). doi: 10.6023/cjoc202000002
	( 叶增辉, 张逢质, 有机化学, 2020, 40,241.)
	(c) Lian, F.; Xu, K. Chin. J. Org. Chem. 2020, 40,3490 (in Chinese). doi: 10.6023/cjoc202000072
	( 廉菲, 徐坤, 有机化学, 2020, 40,3490.)
	(d) Wang, X.; Xu, X.; Wang, Z.; Fang, P.; Mei, T. Chin. J. Org. Chem. 2020, 40,3738 (in Chinese). doi: 10.6023/cjoc202003022
	( 王向阳, 徐学涛, 王振华, 方萍, 梅天胜, 有机化学, 2020, 40,3738.)
	(e) Cheng, X. Chin. J. Org. Chem. 2020, 40,2600 (in Chinese). doi: 10.6023/cjoc202000053
	( 程旭, 有机化学, 2020, 40,2600.)
	(f) Ma, H.; Mei, T. Chin. J. Org. Chem. 2020, 40,3982 (in Chinese). doi: 10.6023/cjoc202000079
	( 马红星, 梅天胜, 有机化学, 2020, 40,3982.)
	(g) Hu, X.; Lei, A. Chin. J. Org. Chem. 2020, 40,3471 (in Chinese). doi: 10.6023/cjoc202000064
	( 胡霞, 雷爱文, 有机化学, 2020, 40,3471.)
[12]	Qian, P.; Su,J. -H.; Wang, Y.; Bi, M.; Zha, Z.; Wang, Z. J. Org. Chem. 2017, 82,6434. doi: 10.1021/acs.joc.7b00635
[13]	Herold, S.; Bafaluy, D.; Muñiz, K. Green Chem. 2018, 20,3191. doi: 10.1039/C8GC01411F
[14]	Hu, X.; Zhang, G.; Bu, F.; Nie, L.; Lei, A. ACS Catal. 2018, 8,9370. doi: 10.1021/acscatal.8b02847
[15]	Wang, H.; Shi, J.; Tan, J.; Xu, W.; Zhang, S.; Xu, K. Org. Lett. 2019, 21,9430. doi: 10.1021/acs.orglett.9b03641
[16]	Xu, K.; Zhang, Z.; Qian, P.; Zha, Z.; Wang, Z. Chem. Commun. 2015, 51,11108. doi: 10.1039/C5CC02730F
[17]	Li, Y.; Gao, H.; Zhang, Z.; Qian, P.; Bi, M.; Zha, Z.; Wang, Z. Chem. Commun. 2016, 52,8600. doi: 10.1039/C6CC03709G
[18]	Wu, J.; Zhou, Y.; Zhou, Y.; Chiang,C. -W.; Lei, A. ACS Catal. 2017, 7,8320. doi: 10.1021/acscatal.7b03551
[19]	Wan, Z.; Wang, D.; Yang, Z.; Zhang, H.; Wang, S.; Lei, A. Green Chem. 2020, 22,3742. doi: 10.1039/D0GC00687D
[20]	Lin,M. -Y.; Xu, K.; Jiang,Y. -Y.; Liu,Y. -G.; Sun,B. -G.; Zeng,C. -C. Adv. Synth. Catal. 2018, 360,1665. doi: 10.1002/adsc.v360.8
[21]	Qian, P.; Yan, Z.; Zhou, Z.; Hu, K.; Wang, J.; Li, Z.; Zha, Z.; Wang, Z. Org. Lett. 2018, 20,6359. doi: 10.1021/acs.orglett.8b02578
[22]	Lian, F.; Sun, C.; Xu, K.; Zeng, C. Org. Lett. 2019, 21,156. doi: 10.1021/acs.orglett.8b03624
[23]	Wu,Z. -J.; Li,S. -R.; Xu,H. -C. Angew. Chem.,Int. Ed. 2018, 57,14070. doi: 10.1002/anie.201807683
[24]	Hu, K.; Qian, P.; Su,J. -H.; Li, Z.; Wang, J.; Zha, Z.; Wang, Z. J. Org. Chem. 2019, 84,1647. doi: 10.1021/acs.joc.8b02930
[25]	Liu, K.; Song, C.; Wu, J.; Deng, Y.; Tang, S.; Lei, A. Green Chem. 2019, 21,765. doi: 10.1039/C8GC03786H
[26]	Feng,M. -L.; Li,S. -Q.; He,H. -Z.; Xi,L. -Y.; Chen,S. -Y.; Yu,X. -Q. Green Chem. 2019, 21,1619. doi: 10.1039/C8GC03622E
[27]	Sun,C. C.; Lian, F.; Xu, K.; Zeng,C. C.; Sun,B. G. Adv. Synth. Catal. 2019, 361,4041. doi: 10.1002/adsc.v361.17
[28]	Hayashi, R.; Shimizu, A.; Song, Y.; Ashikari, Y.; Nokami, T.; Yoshida,J. -I. Chem.-Eur. J. 2017, 23,61. doi: 10.1002/chem.201604484
[29]	Hou,Z. -W.; Liu,D. -J.; Xiong, P.; Lai,X. -L.; Song, J.; Xu,H. -C. Angew. Chem.,Int. Ed. 2021, 60,2943. doi: 10.1002/anie.v60.6
[30]	Niu, L.; Jiang, C.; Liang, Y.; Liu, D.; Bu, F.; Shi, R.; Chen, H.; Chowdhury,A. D.; Lei, A. J. Am. Chem. Soc. 2020, 142,17693. doi: 10.1021/jacs.0c08437
[31]	Zhu, L.; Xiong, P.; Mao,Z. -Y.; Wang,Y. -H.; Yan, X.; Lu, X.; Xu,H. -C. Angew. Chem.,Int. Ed. 2016, 55,2226. doi: 10.1002/anie.201510418
[32]	Folgueiras-Amador,A. A.; Philipps, K.; Guilbaud, S.; Poelakker, J.; Wirth, T. Angew. Chem.,Int. Ed. 2017, 56,15446. doi: 10.1002/anie.201709717
[33]	Xiong, P.; Xu,H. -H.; Xu,H. -C. J. Am. Chem. Soc. 2017, 139,2956. doi: 10.1021/jacs.7b01016
[34]	Hou,Z. W.; Yan, H.; Song,J. S.; Xu,H. C. Chin. J. Chem. 2018, 36,909. doi: 10.1002/cjoc.v36.10
[35]	Long, H.; Song, J.; Xu,H. -C. Org. Chem. Front. 2018, 5,3129. doi: 10.1039/C8QO00803E
[36]	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
[37]	Zhao,H. B.; Xu, P.; Song, J.; Xu,H. C. Angew. Chem.,Int. Ed. 2018, 57,15153. doi: 10.1002/anie.v57.46
[38]	Zhang, S.; Li, L.; Xue, M.; Zhang, R.; Xu, K.; Zeng, C. Org. Lett. 2018, 20,3443. doi: 10.1021/acs.orglett.8b00981
[39]	Liu, C.; Jiang, Q.; Lin, Y.; Fang, Z.; Guo, K. Org. Lett. 2020, 22,795. doi: 10.1021/acs.orglett.9b04141
[40]	Morofuji, T.; Shimizu, A.; Yoshida,J. -I. Chem.-Eur. J. 2015, 21,3211. doi: 10.1002/chem.v21.8
[41]	Zhao,H. B.; Liu,Z. J.; Song, J.; Xu,H. C. Angew. Chem.,Int. Ed. 2017, 56,12732. doi: 10.1002/anie.v56.41
[42]	Hu, K.; Zhang, Y.; Zhou, Z.; Yang, Y.; Zha, Z.; Wang, Z. Org. Lett. 2020, 22,5773. doi: 10.1021/acs.orglett.0c01821
[43]	Guo, S.; Liu, L.; Hu, K.; Sun, Q.; Zha, Z.; Yang, Y.; Wang, Z. Chin. Chem. Lett. 2021, 32,1033. doi: 10.1016/j.cclet.2020.09.041
[44]	Chen, J.; Yan,W. -Q.; Lam,C. M.; Zeng,C. -C.; Hu,L. -M.; Little, R. D. Org. Lett. 2015, 17,986.
[45]	Li,K. J.; Xu, K.; Liu,Y. G.; Zeng,C. C.; Sun,B. G. Adv. Synth. Catal. 2019, 361,1033. doi: 10.1002/adsc.v361.5
[46]	Hu, X.; Zhang, G.; Nie, L.; Kong, T.; Lei, A. Nat. Commun. 2019, 10,5467. doi: 10.1038/s41467-019-13524-4
[47]	Wang, Q.; Wang, P.; Gao, X.; Wang, D.; Wang, S.; Liang,X. -A.; Wang, L.; Zhang, H.; Lei, A. Chem. Sci. 2020, 11,2181. doi: 10.1039/C9SC05729C
[48]	Ye,Z. H.; Ding,M. R.; Wu,Y. Q.; Li, Y.; Hua,W. K.; Zhang,F. Z. Green Chem. 2018, 20,1732. doi: 10.1039/C7GC03739B
[49]	Tang, S.; Wang, S.; Liu, Y.; Cong, H.; Lei, A. Angew. Chem.,Int. Ed. 2018, 57,4737. doi: 10.1002/anie.201800240
[50]	Song, C.; Liu, K.; Wang, Z.; Ding, B.; Wang, S.; Weng, Y.; Chiang,C. -W.; Lei, A. Chem. Sci. 2019, 10,7982. doi: 10.1039/C9SC02218J
[51]	Wesenberg,L. J.; Herold, S.; Shimizu, A.; Yoshida,J. -I.; Waldvogel,S. R. Chem.-Eur. J. 2017, 23,12096. doi: 10.1002/chem.201701979
[52]	Zhang,Y. -Z.; Mo,Z. -Y.; Wang,H. -S.; Wen,X. -A.; Tang,H. -T.; Pan,Y. -M. Green Chem. 2019, 21,3807. doi: 10.1039/C9GC01201J
[53]	Wang,J. -H.; Lei, T.; Nan,X. -L.; Wu,H. -L.; Li,X. -B.; Chen, B.; Tung,C. -H.; Wu,L. -Z. Org. Lett. 2019, 21,5581. doi: 10.1021/acs.orglett.9b01910
[54]	Adeli, Y.; Huang, K.; Liang, Y.; Jiang, Y.; Liu, J.; Song, S.; Zeng,C. -C.; Jiao, N. ACS Catal. 2019, 9,2063. doi: 10.1021/acscatal.8b04351
[55]	Li, J.; Huang, W.; Chen, J.; He, L.; Cheng, X.; Li, G. Angew. Chem.,Int. Ed. 2018, 57,5695. doi: 10.1002/anie.201801106
[56]	Cai,C. -Y.; Shu,X. -M.; Xu,H. -C. Nat. Commun. 2019, 10,4953. doi: 10.1038/s41467-019-13024-5
[57]	Yu, Y.; Yuan, Y.; Liu, H.; He, M.; Yang, M.; Liu, P.; Yu, B.; Dong, X.; Lei, A. Chem. Commun. 2019, 55,1809. doi: 10.1039/C8CC09899A
[58]	Liu, K.; Tang, S.; Wu, T.; Wang, S.; Zou, M.; Cong, H.; Lei, A. Nat. Commun. 2019, 10,639. doi: 10.1038/s41467-019-08414-8
[59]	Fu, N.; Sauer,G. S.; Saha, A.; Loo, A.; Lin, S. Science 2017, 357,575. doi: 10.1126/science.aan6206
[60]	Gao, X.; Wang, P.; Zeng, L.; Tang, S.; Lei, A. J. Am. Chem. Soc. 2018, 140,4195. doi: 10.1021/jacs.7b13049
[61]	Zhang,S. -K.; Samanta,R. C.; Sauermann, N.; Ackermann, L. Chem.-Eur. J. 2018, 24,19166. doi: 10.1002/chem.v24.72
[62]	Sauermann, N.; Mei, R.; Ackermann, L. Angew. Chem.,Int. Ed. 2018, 57,5090. doi: 10.1002/anie.201802206
[63]	Kathiravan, S.; Suriyanarayanan, S.; Nicholls,I. A. Org. Lett. 2019, 21,1968. doi: 10.1021/acs.orglett.9b00003
[64]	Yang,Q. -L.; Wang,X. -Y.; Lu,J. -Y.; Zhang,L. -P.; Fang, P.; Mei,T. -S. J. Am. Chem. Soc. 2018, 140,11487. doi: 10.1021/jacs.8b07380
[65]	Hou,Z. W.; Mao,Z. Y.; Zhao,H. B.; Melcamu,Y. Y.; Lu, X.; Song, J.; Xu,H. C. Angew. Chem.,Int. Ed. 2016, 55,9168. doi: 10.1002/anie.v55.32
[66]	Hou,Z. -W.; Mao,Z. -Y.; Song, J.; Xu,H. -C. ACS Catal. 2017, 7,5810. doi: 10.1021/acscatal.7b02105
[67]	Hou,Z. -W.; Mao,Z. -Y.; Melcamu,Y. Y.; Lu, X.; Xu,H. -C. Angew. Chem.,Int. Ed. 2018, 57,1636. doi: 10.1002/anie.v57.6
[68]	Xu, F.; Long, H.; Song, J.; Xu, H-C. Angew. Chem., Int. Ed. 2019, 58,9017. doi: 10.1002/anie.v58.27
[69]	Tian, C.; Massignan, L.; Meyer,T. H.; Ackermann, L. Angew. Chem.,Int. Ed. 2018, 57,2383. doi: 10.1002/anie.201712647
[70]	Meyer,T. H.; Oliveira,J. o.C.; Sau,S. C.; Ang,N. W.; Ackermann, L. ACS Catal. 2018, 8,9140. doi: 10.1021/acscatal.8b03066
[71]	Mei, R.; Sauermann, N.; Oliveira,J. O.C.; Ackermann, L. J. Am. Chem. Soc. 2018, 140,7913. doi: 10.1021/jacs.8b03521
[72]	Mei, R.; Ma, W.; Zhang, Y.; Guo, X.; Ackermann, L. Org. Lett. 2019, 21,6534. doi: 10.1021/acs.orglett.9b02463
[73]	Kong,W. -J.; Finger,L. H.; Messinis,A. M.; Kuniyil, R.; Oliveira,J. C.A.; Ackermann, L. J. Am. Chem. Soc. 2019, 141,17198. doi: 10.1021/jacs.9b07763
[74]	Wu,Z. -J.; Su, F.; Lin, W.; Song, J.; Wen,T. -B.; Zhang,H. -J.; Xu,H. -C. Angew. Chem.,Int. Ed. 2019, 58,16770. doi: 10.1002/anie.v58.47
[75]	Kong,W. -J.; Shen, Z.; Finger,L. H.; Ackermann, L. Angew. Chem.,Int. Ed. 2020, 59,5551. doi: 10.1002/anie.v59.14
[76]	Xu, F.; Li,Y. -J.; Huang, C.; Xu,H. -C. ACS Catal. 2018, 8,3820. doi: 10.1021/acscatal.8b00373
[77]	Wang,Z. -Q.; Hou, C.; Zhong,Y. -F.; Lu,Y. -X.; Mo,Z. -Y.; Pan,Y. -M.; Tang,H. -T. Org. Lett. 2019, 21,9841. doi: 10.1021/acs.orglett.9b03682
[78]	Cao, Y.; Yuan, Y.; Lin, Y.; Jiang, X.; Weng, Y.; Wang, T.; Bu, F.; Zeng, L.; Lei, A. Green Chem. 2020, 22,1548. doi: 10.1039/D0GC00289E
[79]	Zeng, L.; Li, H.; Hu, J.; Zhang, D.; Hu, J.; Peng, P.; Wang, S.; Shi, R.; Peng, J.; Pao,C. -W.; Chen,J. -L.; Lee,J. -F.; Zhang, H.; Chen,Y. -H.; Lei, A. Nat. Catal. 2020, 3,438. doi: 10.1038/s41929-020-0443-z

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