Chinese Journal of Organic Chemistry >
Recent Advances in the Electrochemical Formation of Carbon-Nitrogen Bonds
Received date: 2020-12-06
Revised date: 2021-02-23
Online published: 2021-03-09
Supported by
Anhui Provincial Natural Science Foundation(2008085MB50); Beijing Education Committee Project(KM202110005006); Graduate Innovation Foundation of Anhui University of Science and Technology(2019CX2057)
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
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 . DOI: 10.6023/cjoc202012013
| [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. |
| [5] | (b) Sambiagio, C.; Marsden,S. P.; Blacker,A. J.; McGowan,P. C. Chem. Soc. Rev. 2014, 43,3525. |
| [5] | (c) Ruiz-Castillo, P.; Buchwald,S. L. Chem. Rev. 2016, 116,12564. |
| [5] | (d) Duan, X.; Liu, N.; Wang, J.; Ma, J. Chin. J. Org. Chem. 2019, 39,661 (in Chinese). |
| [5] | ( 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). |
| [6] | ( 赵金钵, 张前, 王佳, 化学学报. 2015, 73,1235.) |
| [6] | (b) Europe, P. Chem. Rev. 2016, 116,12564. |
| [6] | (c) Baeten, M.; Maes,B. U.W. Adv. Organomet. Chem. 2017, 67,401. |
| [6] | (d) Luo, J.; Wei,W. T. Adv. Synth. Catal. 2018, 360,2076. |
| [6] | (e) Wang, P.; Deng, L. Chin. J. Chem. 2018, 36,1222. |
| [6] | (f) Liu, Q.; Lv, Y.; Bao, P.; Yue, H.; Wei, W. Chin. J. Org. Chem. 2020, 40,4015 (in Chinese). |
| [6] | ( 刘启顺, 吕玉芬, 鲍鹏丽, 岳会兰, 魏伟, 有机化学. 2020, 40,4015.) |
| [6] | (g) Hua, B.; Yang, Q.; Xiao, W. Chin. J. Org. Chem. 2020, 40,3559 (in Chinese). |
| [6] | ( 华庭碧, 阳青青, 肖文精, 有机化学. 2020, 40,3559.) |
| [6] | (h) Dong, K.; Liu, Q.; Wu,L. -Z. Acta Chim. Sinica 2020, 78,299 (in Chinese). |
| [6] | ( 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. |
| [8] | Francke, R.; Little,R. D. Chem. Soc. Rev. 2014, 43,2492. |
| [9] | (a) |
| [9] | (b) Horn,E. J.; Rosen,B. R.; Baran,P. S. ACS Cent. Sci. 2016, 2,302. |
| [9] | (c) Dou,G. Y.; Jiang,Y. Y.; Xu, K.; Zeng,C. C. Org. Chem. Front. 2019, 6,2392. |
| [9] | (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. |
| [10] | (b) Yuan, Y.; Lei,A. W. Acc. Chem. Res. 2019, 52,3309. |
| [10] | (c) Ackermann, L. Acc. Chem. Res. 2020, 53,84. |
| [10] | (d) Jiao,K. -J.; Xing,Y. -K.; Yang,Q. -L.; Qiu, H.; Mei,T. -S. Acc. Chem. Res. 2020, 53,300. |
| [11] | (a) Jiang,Y. Y.; Xu, K.; Zeng,C. C. Chem. Rev. 2018, 118,4485. |
| [11] | (b) Ye, Z.; Zhang, F. Chin. J. Org. Chem. 2020, 40,241 (in Chinese). |
| [11] | ( 叶增辉, 张逢质, 有机化学, 2020, 40,241.) |
| [11] | (c) Lian, F.; Xu, K. Chin. J. Org. Chem. 2020, 40,3490 (in Chinese). |
| [11] | ( 廉菲, 徐坤, 有机化学, 2020, 40,3490.) |
| [11] | (d) Wang, X.; Xu, X.; Wang, Z.; Fang, P.; Mei, T. Chin. J. Org. Chem. 2020, 40,3738 (in Chinese). |
| [11] | ( 王向阳, 徐学涛, 王振华, 方萍, 梅天胜, 有机化学, 2020, 40,3738.) |
| [11] | (e) Cheng, X. Chin. J. Org. Chem. 2020, 40,2600 (in Chinese). |
| [11] | ( 程旭, 有机化学, 2020, 40,2600.) |
| [11] | (f) Ma, H.; Mei, T. Chin. J. Org. Chem. 2020, 40,3982 (in Chinese). |
| [11] | ( 马红星, 梅天胜, 有机化学, 2020, 40,3982.) |
| [11] | (g) Hu, X.; Lei, A. Chin. J. Org. Chem. 2020, 40,3471 (in Chinese). |
| [11] | ( 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. |
| [13] | Herold, S.; Bafaluy, D.; Muñiz, K. Green Chem. 2018, 20,3191. |
| [14] | Hu, X.; Zhang, G.; Bu, F.; Nie, L.; Lei, A. ACS Catal. 2018, 8,9370. |
| [15] | Wang, H.; Shi, J.; Tan, J.; Xu, W.; Zhang, S.; Xu, K. Org. Lett. 2019, 21,9430. |
| [16] | Xu, K.; Zhang, Z.; Qian, P.; Zha, Z.; Wang, Z. Chem. Commun. 2015, 51,11108. |
| [17] | Li, Y.; Gao, H.; Zhang, Z.; Qian, P.; Bi, M.; Zha, Z.; Wang, Z. Chem. Commun. 2016, 52,8600. |
| [18] | Wu, J.; Zhou, Y.; Zhou, Y.; Chiang,C. -W.; Lei, A. ACS Catal. 2017, 7,8320. |
| [19] | Wan, Z.; Wang, D.; Yang, Z.; Zhang, H.; Wang, S.; Lei, A. Green Chem. 2020, 22,3742. |
| [20] | Lin,M. -Y.; Xu, K.; Jiang,Y. -Y.; Liu,Y. -G.; Sun,B. -G.; Zeng,C. -C. Adv. Synth. Catal. 2018, 360,1665. |
| [21] | Qian, P.; Yan, Z.; Zhou, Z.; Hu, K.; Wang, J.; Li, Z.; Zha, Z.; Wang, Z. Org. Lett. 2018, 20,6359. |
| [22] | Lian, F.; Sun, C.; Xu, K.; Zeng, C. Org. Lett. 2019, 21,156. |
| [23] | Wu,Z. -J.; Li,S. -R.; Xu,H. -C. Angew. Chem.,Int. Ed. 2018, 57,14070. |
| [24] | Hu, K.; Qian, P.; Su,J. -H.; Li, Z.; Wang, J.; Zha, Z.; Wang, Z. J. Org. Chem. 2019, 84,1647. |
| [25] | Liu, K.; Song, C.; Wu, J.; Deng, Y.; Tang, S.; Lei, A. Green Chem. 2019, 21,765. |
| [26] | Feng,M. -L.; Li,S. -Q.; He,H. -Z.; Xi,L. -Y.; Chen,S. -Y.; Yu,X. -Q. Green Chem. 2019, 21,1619. |
| [27] | Sun,C. C.; Lian, F.; Xu, K.; Zeng,C. C.; Sun,B. G. Adv. Synth. Catal. 2019, 361,4041. |
| [28] | Hayashi, R.; Shimizu, A.; Song, Y.; Ashikari, Y.; Nokami, T.; Yoshida,J. -I. Chem.-Eur. J. 2017, 23,61. |
| [29] | Hou,Z. -W.; Liu,D. -J.; Xiong, P.; Lai,X. -L.; Song, J.; Xu,H. -C. Angew. Chem.,Int. Ed. 2021, 60,2943. |
| [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. |
| [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. |
| [32] | Folgueiras-Amador,A. A.; Philipps, K.; Guilbaud, S.; Poelakker, J.; Wirth, T. Angew. Chem.,Int. Ed. 2017, 56,15446. |
| [33] | Xiong, P.; Xu,H. -H.; Xu,H. -C. J. Am. Chem. Soc. 2017, 139,2956. |
| [34] | Hou,Z. W.; Yan, H.; Song,J. S.; Xu,H. C. Chin. J. Chem. 2018, 36,909. |
| [35] | Long, H.; Song, J.; Xu,H. -C. Org. Chem. Front. 2018, 5,3129. |
| [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. |
| [37] | Zhao,H. B.; Xu, P.; Song, J.; Xu,H. C. Angew. Chem.,Int. Ed. 2018, 57,15153. |
| [38] | Zhang, S.; Li, L.; Xue, M.; Zhang, R.; Xu, K.; Zeng, C. Org. Lett. 2018, 20,3443. |
| [39] | Liu, C.; Jiang, Q.; Lin, Y.; Fang, Z.; Guo, K. Org. Lett. 2020, 22,795. |
| [40] | Morofuji, T.; Shimizu, A.; Yoshida,J. -I. Chem.-Eur. J. 2015, 21,3211. |
| [41] | Zhao,H. B.; Liu,Z. J.; Song, J.; Xu,H. C. Angew. Chem.,Int. Ed. 2017, 56,12732. |
| [42] | Hu, K.; Zhang, Y.; Zhou, Z.; Yang, Y.; Zha, Z.; Wang, Z. Org. Lett. 2020, 22,5773. |
| [43] | Guo, S.; Liu, L.; Hu, K.; Sun, Q.; Zha, Z.; Yang, Y.; Wang, Z. Chin. Chem. Lett. 2021, 32,1033. |
| [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. |
| [46] | Hu, X.; Zhang, G.; Nie, L.; Kong, T.; Lei, A. Nat. Commun. 2019, 10,5467. |
| [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. |
| [48] | Ye,Z. H.; Ding,M. R.; Wu,Y. Q.; Li, Y.; Hua,W. K.; Zhang,F. Z. Green Chem. 2018, 20,1732. |
| [49] | Tang, S.; Wang, S.; Liu, Y.; Cong, H.; Lei, A. Angew. Chem.,Int. Ed. 2018, 57,4737. |
| [50] | Song, C.; Liu, K.; Wang, Z.; Ding, B.; Wang, S.; Weng, Y.; Chiang,C. -W.; Lei, A. Chem. Sci. 2019, 10,7982. |
| [51] | Wesenberg,L. J.; Herold, S.; Shimizu, A.; Yoshida,J. -I.; Waldvogel,S. R. Chem.-Eur. J. 2017, 23,12096. |
| [52] | Zhang,Y. -Z.; Mo,Z. -Y.; Wang,H. -S.; Wen,X. -A.; Tang,H. -T.; Pan,Y. -M. Green Chem. 2019, 21,3807. |
| [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. |
| [54] | Adeli, Y.; Huang, K.; Liang, Y.; Jiang, Y.; Liu, J.; Song, S.; Zeng,C. -C.; Jiao, N. ACS Catal. 2019, 9,2063. |
| [55] | Li, J.; Huang, W.; Chen, J.; He, L.; Cheng, X.; Li, G. Angew. Chem.,Int. Ed. 2018, 57,5695. |
| [56] | Cai,C. -Y.; Shu,X. -M.; Xu,H. -C. Nat. Commun. 2019, 10,4953. |
| [57] | Yu, Y.; Yuan, Y.; Liu, H.; He, M.; Yang, M.; Liu, P.; Yu, B.; Dong, X.; Lei, A. Chem. Commun. 2019, 55,1809. |
| [58] | Liu, K.; Tang, S.; Wu, T.; Wang, S.; Zou, M.; Cong, H.; Lei, A. Nat. Commun. 2019, 10,639. |
| [59] | Fu, N.; Sauer,G. S.; Saha, A.; Loo, A.; Lin, S. Science 2017, 357,575. |
| [60] | Gao, X.; Wang, P.; Zeng, L.; Tang, S.; Lei, A. J. Am. Chem. Soc. 2018, 140,4195. |
| [61] | Zhang,S. -K.; Samanta,R. C.; Sauermann, N.; Ackermann, L. Chem.-Eur. J. 2018, 24,19166. |
| [62] | Sauermann, N.; Mei, R.; Ackermann, L. Angew. Chem.,Int. Ed. 2018, 57,5090. |
| [63] | Kathiravan, S.; Suriyanarayanan, S.; Nicholls,I. A. Org. Lett. 2019, 21,1968. |
| [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. |
| [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. |
| [66] | Hou,Z. -W.; Mao,Z. -Y.; Song, J.; Xu,H. -C. ACS Catal. 2017, 7,5810. |
| [67] | Hou,Z. -W.; Mao,Z. -Y.; Melcamu,Y. Y.; Lu, X.; Xu,H. -C. Angew. Chem.,Int. Ed. 2018, 57,1636. |
| [68] | Xu, F.; Long, H.; Song, J.; Xu, H-C. Angew. Chem., Int. Ed. 2019, 58,9017. |
| [69] | Tian, C.; Massignan, L.; Meyer,T. H.; Ackermann, L. Angew. Chem.,Int. Ed. 2018, 57,2383. |
| [70] | Meyer,T. H.; Oliveira,J. o.C.; Sau,S. C.; Ang,N. W.; Ackermann, L. ACS Catal. 2018, 8,9140. |
| [71] | Mei, R.; Sauermann, N.; Oliveira,J. O.C.; Ackermann, L. J. Am. Chem. Soc. 2018, 140,7913. |
| [72] | Mei, R.; Ma, W.; Zhang, Y.; Guo, X.; Ackermann, L. Org. Lett. 2019, 21,6534. |
| [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. |
| [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. |
| [75] | Kong,W. -J.; Shen, Z.; Finger,L. H.; Ackermann, L. Angew. Chem.,Int. Ed. 2020, 59,5551. |
| [76] | Xu, F.; Li,Y. -J.; Huang, C.; Xu,H. -C. ACS Catal. 2018, 8,3820. |
| [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. |
| [78] | Cao, Y.; Yuan, Y.; Lin, Y.; Jiang, X.; Weng, Y.; Wang, T.; Bu, F.; Zeng, L.; Lei, A. Green Chem. 2020, 22,1548. |
| [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. |
/
| 〈 |
|
〉 |
