Citation: Pan Zhou, Ting Zou, Hong-Jian Song, Yu-Xiu Liu, Qing-Min Wang. Advances in organoelectrochemical copper-catalyzed reactions[J]. Chinese Chemical Letters, ;2026, 37(1): 111673. doi: 10.1016/j.cclet.2025.111673 shu

Advances in organoelectrochemical copper-catalyzed reactions

State Key Laboratory of Elemento-Organic Chemistry, Research Institute of ElementoOrganic Chemistry, College of Chemistry, Frontiers Science Center for New Organic Matter, Nankai University, Tianjin 300071, China

Received Date: 28 May 2025
Revised Date: 19 July 2025
Accepted Date: 4 August 2025
Available Online: 6 August 2025

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The combination of electrochemistry and metal catalysts has been a popular research topic in the field of organic synthesis due to the abundance and controllable valence states of transition metals, where electron transfer at the electrode produces catalysts with more valence states. Among these transition metal catalysts, electrochemical conversions catalyzed by inexpensive copper metals have received considerable attention. This article systematically investigated this field and reviewed the electrochemical copper catalytic methods applied in organic synthesis from the different activation modes of substrates, which can be broadly classified into the functionalization of C = C bonds, C−H bond activation, C−C and C−X bond activation, and so on.
- Electrochemistry,
- Transition metal catalysis,
- Copper catalysis,
- Copper electrocatalysis
1. [1]
  A. Volta, Phil. Trans. R. Soc. Lond. 90 (1800) 403–431.
2. [2]
  M. Faraday, Ann. Phys. 109 (1834) 433–451. doi: 10.1002/andp.18341092307
3. [3]
  H. Kolbe, Ann. Chem. Pharm. 64 (1848) 339–341. doi: 10.1002/jlac.18480640346
4. [4]
  H. Moissan, Comptesrendushebdomadaires des sé Ances de l'Académiedes Sciences 102 (1886) 1543–1544.
5. [5]
  H.I. Davy, Phil. Trans. R. Soc. Lond. 98 (1808) 1–44.
6. [6]
  M.M. Baizer, J. Electrochem. Soc. 111 (1964) 215. doi: 10.1149/1.2426086
7. [7]
  T. Shono, Tetrahedron 40 (1984) 811–850. doi: 10.1016/S0040-4020(01)91472-3
8. [8]
  J.H. Simons, J. Electrochem. Soc. 95 (1949) 47. doi: 10.1149/1.2776733
9. [9]
  E.J. Corey, R.R. Sauers, J. Am. Chem. Soc. 81 (1959) 1739–1743. doi: 10.1021/ja01516a054
10. [10]
  B.A. Frontana-Uribe, R.D. Little, J.G. Ibanez, et al., Green Chem. 12 (2010) 2099–2119. doi: 10.1039/c0gc00382d
11. [11]
  C. Ma, P. Fang, Z.R. Liu, et al., Sci. Bull. 66 (2021) 2412–2429. doi: 10.1016/j.scib.2021.07.011
12. [12]
  L.F.T. Novaes, J. Liu, Y. Shen, et al., Chem. Soc. Rev. 50 (2021) 7941–8002. doi: 10.1039/d1cs00223f
13. [13]
  E.J. Horn, B.R. Rosen, P.S. Baran, ACS Cent. Sci. 2 (2016) 302–308. doi: 10.1021/acscentsci.6b00091
14. [14]
  J. Yoshida, K. Kataoka, R. Horcajada, et al., Chem. Rev. 108 (2008) 2265–2299. doi: 10.1021/cr0680843
15. [15]
  J.C. Siu, N. Fu, S. Lin, Acc. Chem. Res. 53 (2020) 547–560. doi: 10.1021/acs.accounts.9b00529
16. [16]
  K. Yamamoto, M. Kuriyama, O. Onomura, Acc. Chem. Res. 53 (2019) 105–120. doi: 10.15261/serdj.26.105
17. [17]
  N.W.J. Ang, J.C.A. Oliveira, L. Ackermann, et al., Angew. Chem. Int. Ed. 59 (2020) 12842–12847. doi: 10.1002/anie.202003218
18. [18]
  B.R. Rosen, E.W. Werner, A.G. O'Brien, P.S. Baran, et al., J. Am. Chem. Soc. 136 (2014) 5571–5574. doi: 10.1021/ja5013323
19. [19]
  K.J. Jiao, D. Liu, H.X. Ma, et al., Angew. Chem. Int. Ed. 59 (2020) 6520–6524. doi: 10.1002/anie.201912753
20. [20]
  Z. Duan, L. Zhang, W. Zhang, et al., ACS Catal. 10 (2020) 3828–3831. doi: 10.1021/acscatal.0c00103
21. [21]
  L. Niu, C. Jiang, Y. Liang, et al., J. Am. Chem. Soc. 142 (2020) 17693–17702. doi: 10.1021/jacs.0c08437
22. [22]
  H. Yan, Z.W. Hou, H.C. Xu, et al., Angew. Chem. Int. Ed. 58 (2019) 4592–4595. doi: 10.1002/anie.201814488
23. [23]
  M. Elsherbini, T. Wirth, Acc. Chem. Res. 52 (2019) 3287–3296. doi: 10.1021/acs.accounts.9b00497
24. [24]
  C. Huang, X.X. Qian, H.C. Xu, Angew. Chem. Int. Ed. 58 (2019) 6650–6653. doi: 10.1002/anie.201901610
25. [25]
  J. Hartwig (Ed.), Organotransition Metal Chemistry: from Bonding to Catalysis, University Science Books, New York, 2010.
26. [26]
  K.L. Skubi, T.R. Blum, T.R. Yoon, Chem. Rev. 116 (2016) 10035–10074. doi: 10.1021/acs.chemrev.6b00018
27. [27]
  J. Twilton, C. Le, P. Zhang, et al., Nat. Rev. Chem. 1 (2017) 0052.
28. [28]
  J. Lu, Y. Wang, T. McCallum, N. Fu, et al., iScience 23 (2020) 101796. doi: 10.1016/j.isci.2020.101796
29. [29]
  A.Y. Chan, I.B. Perry, N.B. Bissonnette, et al., Chem. Rev. 122 (2021) 1485–1542.
30. [30]
  R.C. Samanta, T.H. Meyer, I. Siewert, et al., Chem. Sci. 11 (2020) 8657–8670. doi: 10.1039/d0sc03578e
31. [31]
  X. Cheng, A. Lei, T. -S. Mei, et al., CCS Chem. 4 (2022) 1120–1152. doi: 10.31635/ccschem.021.202101451
32. [32]
  C.A. Malapit, M.B. Prater, J.R. Cabrera-Pardo, et al., Chem. Rev. 122 (2022) 3180–3218. doi: 10.1021/acs.chemrev.1c00614
33. [33]
  A. Jutand, Chem. Rev. 108 (2008) 2300–2347. doi: 10.1021/cr068072h
34. [34]
  Y. Kim, W.J. Jang, Beilstein J. Org. Chem. 21 (2025) 155–178. doi: 10.3762/bjoc.21.9
35. [35]
  F. Wang, P. Chen, G. Liu, Nat. Synth. 1 (2022) 107–116. doi: 10.1038/s44160-021-00016-x
36. [36]
  L. Li, Y. Yao, N. Fu, Chem. Catal. 4 (2024) 100898.
37. [37]
  S.E. Allen, R.R. Walvoord, R. Padilla-Salinas, et al., Chem. Rev. 113 (2013) 6234–6458. doi: 10.1021/cr300527g
38. [38]
  N. Fu, L. Song, J. Liu, et al., J. Am. Chem. Soc. 141 (2019) 14480–14485. doi: 10.1021/jacs.9b03296
39. [39]
  W. Liu, J.T. Groves, Acc. Chem. Res. 48 (2015) 1727–1735. doi: 10.1021/acs.accounts.5b00062
40. [40]
  C.Y. Cai, Y.T. Zheng, J.F. Li, et al., J. Am. Chem. Soc. 144 (2022) 11980–11985. doi: 10.1021/jacs.2c05126
41. [41]
  H. Kim, S. Kim, J. Am. Chem. Soc. 146 (2024) 22498–22508. doi: 10.1021/jacs.4c06207
42. [42]
  S. Wu, J. Kaur, T.A. Karl, et al., Angew. Chem. Int. Ed. 61 (2022) e202107811. doi: 10.1002/anie.202107811
43. [43]
  H. Huang, K.A. Steiniger, T.H. Lambert, J. Am. Chem. Soc. 144 (2022) 12567–12583. doi: 10.1021/jacs.2c01914
44. [44]
  L. Qian, M. Shi, Chem. Commun. 59 (2023) 3487–3506. doi: 10.1039/d3cc00437f
45. [45]
  X.L. Lai, H.C. Xu, J. Am. Chem. Soc. 145 (2023) 18753–18759. doi: 10.1021/jacs.3c07146
46. [46]
  T.V. RajanBabu, A.L. Casalnuovo, J. Am. Chem. Soc. 114 (1992) 6265–6266. doi: 10.1021/ja00041a066
47. [47]
  J. Wilting, M. Janssen, C. Müller, et al., J. Am. Chem. Soc. 128 (2006) 11374–11375. doi: 10.1021/ja064378u
48. [48]
  A. Falk, A.L. Göderz, H.G. Schmalz, Angew. Chem. Int. Ed. 52 (2013) 1576–1580. doi: 10.1002/anie.201208082
49. [49]
  X. Li, C. You, J. Yang, et al., Angew. Chem. Int. Ed. 58 (2019) 10928–10931. doi: 10.1002/anie.201906111
50. [50]
  H. Zhang, X. Su, K. Dong, Org. Biomol. Chem. 18 (2020) 391–399. doi: 10.1039/c9ob02374g
51. [51]
  L. Song, N. Fu, B.G. Ernst, et al., Nat. Chem. 12 (2020) 747–754. doi: 10.1038/s41557-020-0469-5
52. [52]
  Q.L. Yang, X.Y. Wang, J.Y. Lu, et al., J. Am. Chem. Soc. 140 (2018) 11487–11494. doi: 10.1021/jacs.8b07380
53. [53]
  S. Kathiravan, S. Suriyanarayanan, I.A. Nicholls, Org. Lett. 21 (2019) 1968–1972. doi: 10.1021/acs.orglett.9b00003
54. [54]
  C. Tian, U. Dhawa, A. Scheremetjew, L. Ackermann, et al., ACS Catal. 9 (2019) 7690–7696. doi: 10.1021/acscatal.9b02348
55. [55]
  X. Yang, Q.L. Yang, X.Y. Wang, et al., J. Org. Chem. 85 (2020) 3497–3507. doi: 10.1021/acs.joc.9b03223
56. [56]
  X. Yi, X. Hu, Angew. Chem. Int. Ed. 58 (2019) 4700–4704. doi: 10.1002/anie.201814509
57. [57]
  J. Poater, M. Solà, C. Viñas, F. Teixidor, Angew. Chem. Int. Ed. 53 (2014) 12191–12195. doi: 10.1002/anie.201407359
58. [58]
  R. Núñez, M. Tarrés, A. Ferrer-Ugalde, et al., Chem. Rev. 116 (2016) 14307–14378. doi: 10.1021/acs.chemrev.6b00198
59. [59]
  L. Yang, B.B. Jei, A. Scheremetjew, et al., Chem. Sci. 12 (2021) 12971–12976. doi: 10.1039/d1sc02905c
60. [60]
  T. Cernak, K.D. Dykstra, S. Tyagarajan, et al., Chem. Soc. Rev. 45 (2016) 546–576. doi: 10.1039/C5CS00628G
61. [61]
  Ł. Woźniak, J.F. Tan, Q.H. Nguyen, et al., Chem. Rev. 120 (2020) 10516–10543. doi: 10.1021/acs.chemrev.0c00559
62. [62]
  H.M.L. Davies, R.E.J. Beckwith, Chem. Rev. 103 (2003) 2861–2904. doi: 10.1021/cr0200217
63. [63]
  C.Y. Cai, X.L. Lai, Y. Wang, et al., Nat. Catal. 5 (2022) 943–951. doi: 10.1038/s41929-022-00855-7
64. [64]
  W. Fan, X. Zhao, Y. Deng, et al., J. Am. Chem. Soc. 144 (2022) 21674–21682. doi: 10.1021/jacs.2c09366
65. [65]
  P.S. Gao, X.J. Weng, Z.H. Wang, et al., Angew. Chem. Int. Ed. 59 (2020) 15254–15259. doi: 10.1002/anie.202005099
66. [66]
  Z. He, H.L. Liu, Z.H. Wang, et al., J. Org. Chem. 88 (2023) 6203–6208. doi: 10.1021/acs.joc.3c00223
67. [67]
  R.R. Naredla, D.A. Klumpp, Chem. Rev. 113 (2013) 6905–6948. doi: 10.1021/cr4001385
68. [68]
  H. Wang, K. Liang, W. Xiong, et al., Sci. Adv. 6 (2020) eaaz0590. doi: 10.1126/sciadv.aaz0590
69. [69]
  Q. Lin, Y. Duan, Y. Li, et al., Nat. Commun. 15 (2024) 6900. doi: 10.1038/s41467-024-50945-2
70. [70]
  R. Francke, R.D. Little, Chem. Soc. Rev. 43 (2014) 2492–2521. doi: 10.1039/c3cs60464k
71. [71]
  M. Yan, Y. Kawamata, P.S. Baran, Chem. Rev. 117 (2017) 13230–13319. doi: 10.1021/acs.chemrev.7b00397
72. [72]
  A. Wiebe, T. Gieshoff, S. Möhle, et al., Angew. Chem. Int. Ed. 57 (2018) 5594–5619. doi: 10.1002/anie.201711060
73. [73]
  L. Zeng, J. Wang, D. Wang, et al., Angew. Chem. Int. Ed. 62 (2023) e202309620. doi: 10.1002/anie.202309620
74. [74]
  L. Zeng, Q. Yang, J. Wang, et al., Science 385 (2024) 216–223. doi: 10.1126/science.ado0875
75. [75]
  Y. Abderrazak, A. Bhattacharyya, O. Reiser, Angew. Chem. Int. Ed. 60 (2021) 21100–21115. doi: 10.1002/anie.202100270
76. [76]
  F. Juliá, ChemCatChem 14 (2022) e202200916. doi: 10.1002/cctc.202200916
77. [77]
  X.L. Lai, M. Chen, Y. Wang, et al., J. Am. Chem. Soc. 144 (2022) 20201–20206. doi: 10.1021/jacs.2c09050
78. [78]
  Y. Yuan, J. Yang, J. Zhang, Chem. Sci. 14 (2023) 705–710. doi: 10.1039/d2sc05428k
79. [79]
  K. Yang, Y. Wang, S. Luo, N. Fu, Chem. Eur. J. 29 (2023) e202203962. doi: 10.1002/chem.202203962
80. [80]
  O. Onomura, H. Arimoto, Y. Matsumura, Y. Demizu, Tetrahedron Lett. 48 (2007) 8668–8672. doi: 10.1016/j.tetlet.2007.10.014
81. [81]
  D. Minato, H. Arimoto, Y. Nagasue, et al., Tetrahedron 64 (2008) 6675–6683. doi: 10.1016/j.tet.2008.05.015
82. [82]
  X. Fang, X. Hu, Q.X. Li, et al., Angew. Chem. Int. Ed. 63 (2024) e202418277.
83. [83]
  B.R. Walker, S. Manabe, A.T. Brusoe, C.S. Sevov, J. Am. Chem. Soc. 143 (2021) 6257–6265. doi: 10.1021/jacs.1c02103
84. [84]
  Y.K. Au, H. Lyu, Y. Quan, Z. Xie, J. Am. Chem. Soc. 142 (2020) 6940–6945. doi: 10.1021/jacs.0c02490
85. [85]
  D.E. Blanco, B. Lee, M.A. Modestino, Proc. Natl. Acad. Sci. U. S. A. 116 (2019) 17683–17689. doi: 10.1073/pnas.1909985116
86. [86]
  M. Santi, J. Seitz, R. Cicala, et al., Chem. Eur. J. 25 (2019) 16230–16235. doi: 10.1002/chem.201904711
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3. [3]
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4. [4]
  Wei-Bin Li , Xiao-Chao Huang , Pei Liu , Jie Kong , Guo-Ping Yang . Recent advances in directing group assisted transition metal catalyzed para-selective C-H functionalization. Chinese Chemical Letters, 2025, 36(6): 110543-. doi: 10.1016/j.cclet.2024.110543
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  Wujun Jian , Mong-Feng Chiou , Yajun Li , Hongli Bao , Song Yang . Cu-catalyzed regioselective diborylation of 1,3-enynes for the efficient synthesis of 1,4-diborylated allenes. Chinese Chemical Letters, 2024, 35(5): 108980-. doi: 10.1016/j.cclet.2023.108980
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  Kongchuan Wu , Dandan Lu , Jianbin Lin , Ting-Bin Wen , Wei Hao , Kai Tan , Hui-Jun Zhang . Elucidating ligand effects in rhodium(Ⅲ)-catalyzed arene–alkene coupling reactions. Chinese Chemical Letters, 2024, 35(5): 108906-. doi: 10.1016/j.cclet.2023.108906
7. [7]
  Daheng Wen , Weiwei Fang , Yongmei Liu , Tao Tu . Valorization of carbon dioxide with alcohols. Chinese Chemical Letters, 2024, 35(7): 109394-. doi: 10.1016/j.cclet.2023.109394
8. [8]
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  Yuemin Chen , Yunqi Wu , Guoao Wang , Feihu Cui , Haitao Tang , Yingming Pan . Electricity-driven enantioselective cross-dehydrogenative coupling of two C(sp³)-H bonds enabled by organocatalysis. Chinese Chemical Letters, 2024, 35(9): 109445-. doi: 10.1016/j.cclet.2023.109445
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  Li Li , Zhi-Xin Yan , Chuan-Kun Ran , Yi Liu , Shuo Zhang , Tian-Yu Gao , Long-Fei Dai , Li-Li Liao , Jian-Heng Ye , Da-Gang Yu . Electro-reductive carboxylation of CCl bonds in unactivated alkyl chlorides and polyvinyl chloride with CO₂. Chinese Chemical Letters, 2024, 35(12): 110104-. doi: 10.1016/j.cclet.2024.110104
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  Ruilong Geng , Lingzi Peng , Chang Guo . Dynamic kinetic stereodivergent transformations of propargylic ammonium salts via dual nickel and copper catalysis. Chinese Chemical Letters, 2024, 35(8): 109433-. doi: 10.1016/j.cclet.2023.109433
17. [17]
  Rong-Nan Yi , Wei-Min He . Visible light/copper catalysis enabled radial type ring-opening of sulfonium salts. Chinese Chemical Letters, 2025, 36(4): 110787-. doi: 10.1016/j.cclet.2024.110787
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