Electrochemical Mn-catalyzed nitrogenation of alkynes to nitriles via C≡C bonds cleavage
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* Corresponding authors.
E-mail addresses: aiwenlei@whu.edu.cn (A. Lei), hong.yi@whu.edu.cn (H. Yi).
Citation:
Yuwei Liang, Jianwei Huang, Zhiqiang Zhang, Qinghong Yang, Aiwen Lei, Hong Yi. Electrochemical Mn-catalyzed nitrogenation of alkynes to nitriles via C≡C bonds cleavage[J]. Chinese Chemical Letters,
;2026, 37(4): 111166.
doi:
10.1016/j.cclet.2025.111166
P.S. Baran, J. Am. Chem. Soc. 140 (2018) 4751–4755.
doi: 10.1021/jacs.8b02266
W. Liu, B. Hong, J. Wang, X. Lei, Acc. Chem. Res. 53 (2020) 2569–2586.
doi: 10.1021/acs.accounts.0c00531
A.G. Atanasov, S.B. Zotchev, V.M. Dirsch, C.T. Supuran, Nat. Rev. Drug. Discov. 20 (2021) 200–216.
doi: 10.1038/s41573-020-00114-z
S.H. Kennedy, B.D. Dherange, K.J. Berger, M.D. Levin, Nature 593 (2021) 223–227.
doi: 10.1038/s41586-021-03448-9
Z. Fan, X. Chen, K. Tanaka, et al., Nature 610 (2022) 87–93.
doi: 10.1038/s41586-022-05175-1
C. Hui, Z. Wang, S. Wang, C. Xu, Org. Chem. Front. 9 (2022) 1451–1457.
doi: 10.1039/d2qo00043a
P. Ji, C.C. Davies, F. Gao, et al., Nat. Commun. 13 (2022) 4565.
doi: 10.1038/s41467-022-32201-7
J. Jurczyk, J. Woo, S.F. Kim, et al., Nat. Synth. 1 (2022) 352–364.
doi: 10.1038/s44160-022-00052-1
B.A. Wright, A. Matviitsuk, M.J. Black, et al., J. Am. Chem. Soc. 145 (2023) 10960–10966.
doi: 10.1021/jacs.3c02616
Z. Dong, Z. Ren, S.J. Thompson, Y. Xu, G. Dong, Chem. Rev. 117 (2017) 9333–9403.
doi: 10.1021/acs.chemrev.6b00574
J. He, M. Wasa, K.S. Chan, Q. Shao, J.Q. Yu, Chem. Rev. 117 (2017) 8754–8786.
doi: 10.1021/acs.chemrev.6b00622
Y. Park, Y. Kim, S. Chang, Chem. Rev. 117 (2017) 9247–9301.
doi: 10.1021/acs.chemrev.6b00644
Y. Qin, L. Zhu, S. Luo, Chem. Rev. 117 (2017) 9433–9520.
doi: 10.1021/acs.chemrev.6b00657
Y. Yang, J. Lan, J. You, Chem. Rev. 117 (2017) 8787–8863.
doi: 10.1021/acs.chemrev.6b00567
H. Yi, G. Zhang, H. Wang, et al., Chem. Rev. 117 (2017) 9016–9085.
doi: 10.1021/acs.chemrev.6b00620
P. Gandeepan, T. Müller, D. Zell, et al., Chem. Rev. 119 (2018) 2192–2452.
S.K. Sinha, S. Guin, S. Maiti, et al., Chem. Rev. 122 (2021) 5682–5841.
C.X. Ye, E. Meggers, Acc. Chem. Res. 56 (2023) 1128–1141.
doi: 10.1021/acs.accounts.3c00081
S. Kim, J. Chung, B.M. Kim, Tetrahedron Lett. 52 (2011) 1363–1367.
doi: 10.1016/j.tetlet.2011.01.065
Y. Deng, X.J. Wei, H. Wang, et al., Angew. Chem. Int. Ed. 56 (2017) 832–836.
doi: 10.1002/anie.201607948
Z. Huang, R. Guan, M. Shanmugam, et al., J. Am. Chem. Soc. 143 (2021) 10005–10013.
doi: 10.1021/jacs.1c05757
J. Li, J. Zhao, C. Ma, et al., ChemSusChem 14 (2021) 4985–4992.
doi: 10.1002/cssc.202101504
H. Wang, R. Jia, M. Hong, et al., Green Chem. 23 (2021) 6591–6597.
doi: 10.1039/d1gc01931g
A. Ruffoni, C. Hampton, M. Simonetti, D. Leonori, Nature 610 (2022) 81–86.
doi: 10.1038/s41586-022-05211-0
F. Chen, T. Wang, N. Jiao, Chem. Rev. 114 (2014) 8613–8661.
doi: 10.1021/cr400628s
X. Zhu, J. Liu, W. Zhang, Nat. Chem. Biol. 11 (2015) 115–120.
doi: 10.1038/nchembio.1718
F. Amblard, J.H. Cho, R.F. Schinazi, Chem. Rev. 109 (2009) 4207–4220.
doi: 10.1021/cr9001462
K. Gilmore, I.V. Alabugin, Chem. Rev. 111 (2011) 6513–6556.
doi: 10.1021/cr200164y
R. Dorel, A.M. Echavarren, Chem. Rev. 115 (2015) 9028–9072.
doi: 10.1021/cr500691k
V.P. Boyarskiy, D.S. Ryabukhin, N.A. Bokach, A.V. Vasilyev, Chem. Rev. 116 (2016) 5894–5986.
doi: 10.1021/acs.chemrev.5b00514
T. Shen, T. Wang, C. Qin, N. Jiao, Angew. Chem. Int. Ed. 52 (2013) 6677–6680.
doi: 10.1002/anie.201300193
N. Okamoto, M. Ishikura, R. Yanada, Org. Lett. 15 (2013) 2571–2573.
doi: 10.1021/ol401311h
U. Dutta, D.W. Lupton, D. Maiti, Org. Lett. 18 (2016) 860–863.
doi: 10.1021/acs.orglett.6b00147
Y. Lin, Q. Song, Eur. J. Org. Chem. 2016 (2016) 3056–3059.
doi: 10.1002/ejoc.201600438
D.J. Constable, P.J. Dunn, J.D. Hayler, et al., Green Chem. 9 (2007) 411–420.
doi: 10.1039/B703488C
F. Fleming, Nat. Prod. Rep. 16 (1999) 597–606.
doi: 10.1039/a804370a
F.F. Fleming, L. Yao, P. Ravikumar, L. Funk, B.C. Shook, J. Med. Chem. 53 (2010) 7902–7917.
doi: 10.1021/jm100762r
X. Liu, L. Huang, Y. Ma, et al., Nat. Commun. 15 (2024) 7012.
doi: 10.1038/s41467-024-51307-8
J. Qin, B. Han, X. Liu, et al., Sci. Adv. 8 (2022) eadd1267.
doi: 10.1126/sciadv.add1267
C. Xian, J. He, Y. He, et al., J. Am. Chem. Soc. 144 (2022) 23321–23331.
doi: 10.1021/jacs.2c07061
J.B. Sperry, D.L. Wright, Chem. Soc. Rev. 35 (2006) 605–621.
doi: 10.1039/b512308a
M. Yan, Y. Kawamata, P.S. Baran, Chem. Rev. 117 (2017) 13230–13319.
doi: 10.1021/acs.chemrev.7b00397
Q.L. Yang, P. Fang, T.S. Mei, Chin. J. Chem. 36 (2018) 338–352.
doi: 10.1002/cjoc.201700740
Q. Jing, K.D. Moeller, Acc. Chem. Res. 53 (2019) 135–143.
N. Chen, H.C. Xu, Chem. Rec. 21 (2021) 2306–2319.
doi: 10.1002/tcr.202100048
L.F. Novaes, J. Liu, Y. Shen, et al., Chem. Soc. Rev. 50 (2021) 7941–8002.
doi: 10.1039/d1cs00223f
Z. Yang, W. Shi, H. Alhumade, H. Yi, A. Lei, Nat. Synth. 2 (2023) 217–230.
doi: 10.1038/s44160-022-00221-2
P. Wang, S. Tang, P. Huang, A. Lei, Angew. Chem. 129 (2017) 3055–3059.
doi: 10.1002/ange.201700012
L. Jie, B. Guo, J. Song, H. Xu, J. Am. Chem. Soc. 144 (2022) 2343–2350.
doi: 10.1021/jacs.1c12762
X. Liu, D. Yang, Z. Liu, et al., J. Am. Chem. Soc. 145 (2023) 3175–3186.
doi: 10.1021/jacs.2c12902
N. Fu, G.S. Sauer, A. Saha, A. Loo, S. Lin, Science 357 (2017) 575–579.
doi: 10.1126/science.aan6206
L. Niu, C. Jiang, Y. Liang, et al., J. Am. Chem. Soc. 142 (2020) 17693–17702.
doi: 10.1021/jacs.0c08437
T.H. Meyer, R.C. Samanta, A. Del Vecchio, L. Ackermann, Chem. Sci. 12 (2021) 2890–2897.
doi: 10.1039/d0sc05924b
L.F. Novaes, Y. Wang, J. Liu, et al., ACS Catal. 12 (2022) 14106–14112.
doi: 10.1021/acscatal.2c05186
Y. Wang, L. Li, N. Fu, ACS Catal. 12 (2022) 10661–10667.
doi: 10.1021/acscatal.2c02934
Y. Weng, X. Xu, H. Chen, Y. Zhang, X. Zhuo, Angew. Chem. 134 (2022) e202206308.
doi: 10.1002/ange.202206308
M. Cao, H. Wang, Y. Ma, C.H. Tung, L. Liu, J. Am. Chem. Soc. 144 (2022) 15383–15390.
doi: 10.1021/jacs.2c07089
X. Huang, T.M. Bergsten, J.T. Groves, J. Am. Chem. Soc. 137 (2015) 5300–5303.
doi: 10.1021/jacs.5b01983
L.M. Jin, P. Xu, J. Xie, X.P. Zhang, J. Am. Chem. Soc. 142 (2020) 20828–20836.
doi: 10.1021/jacs.0c10415
X. Kong, Y. Liu, L. Lin, Q. Chen, B. Xu, Green Chem. 21 (2019) 3796–3801.
S. Li, H.W. Du, P.W. Davies, W. Shu, CCS Chem. 6 (2024) 1060–1070.
doi: 10.31635/ccschem.023.202302999
O.M. Mulina, N.V. Zhironkina, S.A. Paveliev, D.V. Demchuk, A.O. Terent’ev, Org. Lett. 22 (2020) 1818–1824.
doi: 10.1021/acs.orglett.0c00139
Y. Ning, X.F. Zhao, Y.B. Wu, X. Bi, Org. Lett. 19 (2017) 6240–6243.
doi: 10.1021/acs.orglett.7b03204
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Pan Zhou , Ting Zou , Hong-Jian Song , Yu-Xiu Liu , Qing-Min Wang . Advances in organoelectrochemical copper-catalyzed reactions. Chinese Chemical Letters, 2026, 37(1): 111673-. doi: 10.1016/j.cclet.2025.111673
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