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CC BY 4.0 · SynOpen 2023; 07(04): 511-520
DOI: 10.1055/a-2184-8411
DOI: 10.1055/a-2184-8411
graphical review
Virtual Collection Electrochemical Organic Synthesis
Electrochemical Synthesis of Organoselenium Compounds: A Graphical Review
This work was funded by the National Natural Science Foundation of China (22271067), the Key-Area Research Project of Guangdong Provincial Department of Education (2022ZDZX2051) and the Plan on Enhancing Scientific Research in Guangzhou Medical University (GMU).
Abstract
Electrochemical synthesis, due to its environmentally benign, sustainable, and practical nature, has become an appealing and powerful substitute for traditional methods for oxidizing and reducing organic compounds. Thus, numerous valuable changes have been established in the field of organic synthesis through the utilization of electrochemistry. Among these electrochemical transformations, the formation of C–Se bonds stands out as an exceptionally noteworthy reaction type. In this graphical review, we present a succinct summary of the progress in utilizing electrochemical strategies for synthesizing organoselenium compounds.
Key words
electrochemistry - organoselenium compounds - selenylation - difunctionalization - cyclization - cross-couplingPublication History
Received: 17 August 2023
Accepted after revision: 21 September 2023
Accepted Manuscript online:
02 October 2023
Article published online:
24 October 2023
© 2023. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/)
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References
- 1a Zhang X, Wang C, Jiang H, Sun L. Chem. Commun. 2018; 54: 8781
- 1b Meirinho AG, Pereira VF, Martins GM, Saba S, Rafique J, Braga AL, Mendes SR. Eur. J. Org. Chem. 2019; 6465
- 1c Lazzaris MJ, Martins GM, Xavier FR, Braga AL, Mendes SR. Eur. J. Org. Chem. 2021; 4411
- 1d Wang Q, Ma X.-L, Chen Y.-Y, Jiang C.-N, Xu Y.-L. Eur. J. Org. Chem. 2020; 4384
- 1e Liu X, Wang Y, Song D, Wang Y, Cao H. Chem. Commun. 2020; 56: 15325
- 1f Yi R.-N, Wu Z.-L, Ouyang W.-T, Wang W.-F, He W.-M. Tetrahedron Lett. 2021; 77: 153257
- 1g Lu F, Hu L, Zhang J, Feng Y. Asian J. Org. Chem. 2023; 12: e202200719
- 1h Wang Z, Wang Y, Zhao M, Wu Q, Liu D, Yi R. Chin. J. Org. Chem. 2021; 41: 3726
- 1i Chen J.-Y, Wu H.-Y, Gui Q.-W, Yan S.-S, Deng J, Lin Y.-W, Cao Z, He W.-M. Chin. J. Catal. 2021; 42: 1445
- 1j Karmakar P, Karmakar I, Pal D, Das S, Brahmachari G. J. Org. Chem. 2023; 88: 1049
- 1k Jat PK, Yadav L, Chouhan A, Ucheniya K, Badsara SS. Chem. Commun. 2023; 59: 5415
- 1l Chen J, Xiao Y, You X, Li S, Fu Y, Ouyang Y. ChemistrySelect 2023; 8: 1049
- 1m Wang Z, Li J, Liu Y, Chen Q, Zhang P, Wu J. Mol. Catal. 2023; 540: 113038
- 1n Lin S, Cheng X, Hasimujiang B, Xu Z, Li F, Ruan Z. Org. Biomol. Chem. 2021; 20: 117
- 1o Wu Z.-L, Chen J.-Y, Tian X.-Z, Ouyang W.-T, Zhang Z.-T, He W.-M. Chin. Chem. Lett. 2021; 33: 1501
- 1p Xu Z, Yao J, Zhong K, Lin S, Hu X, Ruan Z. J. Org. Chem. 2023; 88: 5572
- 2a Sun L, Yuan Y, Yao M, Wang H, Wang D, Gao M, Chen Y.-H, Lei A. Org. Lett. 2019; 21: 1297
- 2b Meng XJ, Zhong PF, Wang YM, Wang HS, Tang HT, Pan YM. Adv. Synth. Catal. 2019; 362: 506
- 2c Kong X, Yu K, Chen Q, Xu B. Asian J. Org. Chem. 2020; 9: 1760
- 2d Sun L, Wang L, Alhumade H, Yi H, Cai H, Lei A. Org. Lett. 2021; 23: 7724
- 2e Hou Z.-W, Li L, Wang L. Org. Chem. Front. 2022; 9: 2815
- 2f Hasimujiang B, Zhu J, Xu W, Wang H, Hu X, Ruan Z. Adv. Synth. Catal. 2023; 365: 2929
- 2g Wu SF, Yu Y, Yuan Y, Li Z, Ye KY. Eur. J. Org. Chem. 2022; e202201032
- 2h Ren S.-Y, Zhou Q, Zhou H.-Y, Wang L.-W, Mulina OM, Paveliev SA, Tang H.-T, Terent’ev AO, Pan Y.-M, Meng X.-J. J. Org. Chem. 2023; 88: 5760
- 2i Zhou Y, Zhang J.-Q, Ren H, Dong Z.-B. J. Org. Chem. 2023; 88: 5321
- 2j Zhou P, Jiao H, Niu K, Song H, Liu Y, Wang Q. ACS Sustainable Chem. Eng. 2023; 11: 2607
- 3a Hua J, Fang Z, Xu J, Bian M, Liu C, He W, Zhu N, Yang Z, Guo K. Green Chem. 2019; 21: 4706
- 3b Wang XY, Zhong YF, Mo ZY, Wu SH, Xu YL, Tang HT, Pan YM. Adv. Synth. Catal. 2021; 363: 208
- 3c Guan Z, Wang Y, Wang H, Huang Y, Wang S, Tang H, Zhang H, Lei A. Green Chem. 2019; 21: 4976
- 3d Mallick S, Baidya M, Mahanty K, Maiti D, De Sarkar S. Adv. Synth. Catal. 2020; 362: 1046
- 3e Kharma A, Jacob C, Bozzi ÍA. O, Jardim GA. M, Braga AL, Salomão K, Gatto CC, Silva MF. S, Pessoa C, Stangier M, Ackermann L, da Silva Júnior EN. Eur. J. Org. Chem. 2020; 4474
- 3f Kim Y, Jang J, Kim DY. Asian J. Org. Chem. 2021; 10: 327
- 3g Wang Y, Xu N, Li W, Li J, Huo Y, Zhu W, Liu Q. Org. Biomol. Chem. 2022; 20: 2813
- 3h Hasimujiang B, Lin S, Zheng C, Zeng Y, Ruan Z. Molecules 2022; 27: 6314
- 3i Doerner CV, Scheide MR, Nicoleti CR, Durigon DC, Idiarte VD, Sousa MJ. A, Mendes SR, Saba S, Neto JS. S, Martins GM, Rafique J, Braga AL. Front. Chem. 2022; 10: 880099
- 3j Cheng X, Hasimujiang B, Xu Z, Cai H, Chen G, Mo G, Ruan Z. J. Org. Chem. 2021; 86: 16045
- 3k Bian M, Hua J, Ma T, Xu J, Cai C, Yang Z, Liu C, He W, Fang Z, Guo K. Org. Biomol. Chem. 2021; 19: 3207
- 3l Lu F, Xu J, Li H, Wang K, Ouyang D, Sun L, Huang M, Jiang J, Hu J, Alhumade H, Lu L, Lei A. Green Chem. 2021; 23: 7982
- 3m Li H, Lu F, Xu J, Hu J, Alhumade H, Lu L, Lei A. Org. Chem. Front. 2022; 9: 2786
- 3n Wu Y, Chen J.-Y, Ning J, Jiang X, Deng J, Deng Y, Xu R, He W.-M. Green Chem. 2021; 23: 3950
- 3o Halder A, Mahanty K, Maiti D, De Sarkar S. Chem. Asian J. 2021; 16: 3895
- 3p Hua J, Fang Z, Bian M, Ma T, Yang M, Xu J, Liu C, He W, Zhu N, Yang Z, Guo K. ChemSusChem 2020; 13: 2053
- 3q Yu K, Kong X, Yang J, Li G, Xu B, Chen Q. J. Org. Chem. 2020; 86: 917
- 3r Maiti D, Halder A, Sasidharan Pillai A, De Sarkar S. J. Org. Chem. 2021; 86: 16084
- 3s Gao W, Li B, Zong L, Yu L, Li X, Li Q, Zhang X, Zhang S, Xu K. Eur. J. Org. Chem. 2021; 2431
- 3t Kim YJ, Kim DY. Org. Lett. 2019; 21: 1021
- 3u Hasimujiang B, Zeng Y, Zou S, Zhong K, Su L, Hu X, Ruan Z. Isr. J. Chem. 2023; e202300088
- 3v Chen WC, Bai R, Cheng WL, Peng CY, Reddy DM, Badsara SS, Lee CF. Org. Biomol. Chem. 2023; 21: 3002
- 3w Dapkekar AB, Satyanarayana G. Chem. Commun. 2023; 59: 8719
- 3x Xiong TK, Xia Q, Zhou XQ, Li SH, Cui FH, Tang HT, Pan YM, Liang Y. Adv. Synth. Catal. 2023; 365: 2183
- 3y Tan P, Lu L, Wang S, Wang J, Chen J, Zhang Y, Xie L, Yang S, Chen J, Zhang Z. J. Org. Chem. 2023; 88: 7245
- 3z Zeng S, Fang S, Cai H, Wang D, Liu W, Hu X, Sun P, Ruan Z. Chem. Asian J. 2022; 17: e202200762
- 4a Chen Z, Wang Y, Hu C, Wang D, Lei P, Yi H, Yuan Y, Lei A. Org. Lett. 2022; 24: 3307
- 4b Fu Z, Yin J, He D, Yi X, Guo S, Cai H. Green Chem. 2022; 24: 130
- 4c Zhang X, Cui T, Zhang Y, Gu W, Liu P, Sun P. Adv. Synth. Catal. 2019; 361: 2014
- 4d Guo S, Li S, Zhang Z, Yan W, Cai H. Tetrahedron Lett. 2020; 61: 151566
- 4e Ucheniya K, Chouhan A, Yadav L, Jat PK, Badsara SS. J. Org. Chem. 2023; 88: 6096