10.1002/chem.202004229
Chemistry - A European Journal
COMMUNICATION
Lett. 2013, 15, 3286–3289; d) T. W. Lyons, M. S. Sanford, Chem. Rev.
2010, 110, 1147–1169, and references cited therein.
[18] a) J. Deng, T. Sanchez, N. Neamati, J. M. Briggs, J. Med. Chem. 2006,
49, 1684–1692; b) K. M. Dalessandri, G. L. Firestone, M. D. Fitch, H.
L. Bradlow, L. F. Bjeldanes, Nutr Cancer. 2004, 50, 161–167; c) R. Bell,
S. Carmeli, N. Sar, J. Nat. Prod. 1994, 57, 1587–1590.
[9]
a) D. Kurandina, D. Yadagiri, M. Rivas, A. Kavun, P. Chuentragool, K.
Hayama, V. Gevorgyan, J. Am. Chem. Soc. 2019, 141, 8104–8109; b) A.
Ruffoni, F. Juliá, T. D. Svejstrup, A. J. Mcmillan, J. J. Douglas, D. Leonori,
Nat. Chem. 2019, 11, 426–433; c) H. Jiang, G. Seidler and A. Studer,
Angew. Chem., Int. Ed., 2019, 58, 16528–16532; d) X. Hu,G. Zhang, L.
Nie, T. Kong, A. Lei, Nat. Commun. 2019, 10, 5467–5476; e) X. Wang,
D. Xia, W. Qin, R. Zhou, X. Zhou, Q. Zhou, W. Liu, X. Dai, H. Wang, S.
Wang, L. Tan, D. Zhang, H. Song, X.-Y. Liu, Y. Qin, Chem 2017, 2, 803–
816; f) E. Ito, T. Fukushima, T. Kawakami, K. Murakami, K. Itami, Chem
2017, 2, 383–392; g) X.-Q. Hu, X. Qi, J.-R. Chen, Q.-Q. Zhao, Q. Wei, Y.
Lan, W.-J. Xiao, Nat. Commun. 2016, 7, 11188–11199; h) H. Kim, T. Kim,
D. G. Lee, S. W. Roh, C. Lee, Chem. Commun. 2014, 50, 9273–9276;i)
B. Giese, J. Dupuis, Angew. Chem., Int. Ed., 1983, 22, 622–623; j) B.
Giese, Angew. Chem., Int. Ed., 1983, 22, 753–764.
[19] a) Y. Gao, G. Lu, P. Zhang, L. Zhang, G. Tang, Y. Zhao, Org. Lett. 2016,
18, 1242–1245; b) H. Egami, T. Ide, Y. Kawato, Y. Hamashima, Chem.
Commun. 2015, 51, 16675–16678.
[10] For reviews on N-centered radicals, see: a) H. Jiang, A. Studer, Chem.
Soc. Rev. 2020, 49, 1790–1811; b) H. Jiang, A. Studer, CCS. Chem.
2019, 1, 38–49; c) H. Yi, G. Zhang, H. Wang, Z. Huang, J. Wang, A. K.
Singh, A. Lei, Chem. Rev. 2017, 117, 9016–9085; d) M. D. Kӓrkӓs, Acs
Catal. 2017, 7, 4999-5022; e) T. Xiong, Q. Zhang, Chem. Soc. Rev. 2016,
45, 3069–3087; f) A. Studer, D. P. Curran, Angew. Chem. Int. Ed. 2016,
55, 58–102; g) J.-R. Chen, X.-Q. Hu, L.-Q. Lu, W.-J. Xiao, Chem. Soc.
Rev. 2016, 45, 2044–2056.
[11] a) D. C. Miller, G. J. Choi, H. S. Orbe, R. R. Knowles, J. Am. Chem. Soc.
2015, 137, 13492–13495; b) G. J. Choi, R. R. Knowles, J. Am. Chem.
Soc. 2015, 137, 9226–9229.
[12] X.-Q. Hu, J.-R. Chen, Q. Wei, F.-L. Liu, Q.-H. Deng, A. M. Beauchemin,
W.-J. Xiao, Angew. Chem. Int. Ed. 2014, 53, 12163–12167.
[13] K. Tong, X. Liu, Y. Zhang, S. Yu, Chem. Eur. J. 2016, 22, 15669–15673.
[14] For reviews on electrochemical C−H functionalization, see: a) T. H.
Meyer, I. Choi, C. Tian, L. Ackermann, Chem 2020, 6, 2484–2496; b) L.
Ackermann, Acc. Chem. Res. 2020, 53, 84–104; c) Q.-L. Yang, P. Fang,
T.-S. Mei, Chin. J. Chem. 2018, 36, 338–352; d) M. D. Kꢀrkꢀs, Chem.
Soc. Rev. 2018, 47, 5786–5865; e) N. Sauermann, T. H. Meyer, L.
Ackermann, Chem. Eur. J. 2018, 24, 16209–16217; f) N. Sauermann, T.
H. Meyer, Y. Qiu, L. Ackermann, ACS Catal. 2018, 8, 7086–7103.
[15] For selected recent examples of electrochemical C−H amidations, see:
a) Y. Kawamata, J. C. Vantourout, D. P. Hickey, P. Bai, L. Chen, Q. Hou,
W. Qiao, K. Barman, M. A. Edwards, A. F. Garrido-Castro, J. N.
deGruyter, H. Nakamura, K. Knouse, C. Qin, K. J. Clay, D. Bao, C. Li, J.
T. Starr, C. Garcia-Irizarry, N. Sach, H. S. White, M. Neurock, S. D.
Minteer, P. S. Baran, J. Am. Chem. Soc. 2019, 141, 6392–6402; b) Y.
Adeli, K. Huang, Y. Liang, Y. Jiang, J. Liu, S. Song, C.-C. Zeng, N. Jiao,
ACS Catal. 2019, 9, 2063–2067; c) J. H. Wang, T. Lei, X. L. Nan, H. L.
Wu, X. B. Li, B. Chen, C. H. Tung, L. Z. Wu, Org. Lett. 2019, 21, 5581–
5585; d) S. Tang, S. Wang, Y. Liu, H. Cong, A. Lei, Angew. Chem., Int.
Ed. 2018, 57, 4737–4741; e) Z.-W. Hou, Z.-Y. Mao, Y. Y. Melcamu, X.
Lu, H.-C. Xu, Angew. Chem., Int. Ed. 2018, 57, 1636–1639; f) X. Gao, P.
Wang, L. Zeng, S. Tang, A. Lei, J. Am. Chem. Soc. 2018, 140, 4195–
4199; g) Q.-L. Yang, X.-Y. Wang, J.-Y. Lu, L.-P. Zhang, P. Fang, T.-S.
Mei, J. Am. Chem. Soc. 2018, 140, 11487–11494; h) F. Xu, Y.-J. Li, C.
Huang, H.-C. Xu, ACS Catal. 2018, 8, 3820–3824; i) T. Gieshoff, A. Kehl,
D. Schollmeyer, K. D. Moeller, S. R. Waldvogel, J. Am. Chem. Soc. 2017,
139, 12317–12324; j) P. Xiong, H.-H. Xu, H.-C. Xu, J. Am. Chem. Soc.
2017, 139, 2956–2959; k) J. Wu, Y. Zhou, Y. Zhou, C.-W. Chiang, A. Lei,
ACS Catal. 2017, 7, 8320–8323; l) C. Li, Y. Kawamata, H. Nakamura, J.
C. Vantourout, Z. Liu, Q. Hou, D. Bao, J. T. Starr, J. Chen, M. Yan, P. S.
Baran, Angew. Chem., Int. Ed. 2017, 56, 13088–13093; m) T. Morofuji,
A. Shimizu, J. Yoshida, J. Am. Chem. Soc. 2015, 137, 9816–9819; n) B.
R. Rosen, E. W. Werner, A. G. ƠBrien, P. S. Baran, J. Am. Chem. Soc.
2014, 136, 5571–5574; o) W. J. Gao, W. C. Li, C. C. Zeng, H. Y. Tian, L.
M. Hu, R. D. Little, J. Org. Chem. 2014, 79, 9613–9618. For reviews,
see: p) R. Francke, R. D. Little, Chem. Soc. Rev. 2014, 43, 2492–2521;
q) A. Jutand, Chem. Rev. 2008, 108, 2300–2347
[16] Y. Qiu, J. Struwe, T. H. Meyer, J. C. A. Oliveira, L. Ackermann, Chem.
Eur. J. 2018, 24, 12784–12789.
[17]
CCDC 2004885.The data can be obtained free of charge from The
Cambridge Crystallographic Data Centre.
5
This article is protected by copyright. All rights reserved.