Electrochemical Synthesis of Organoselenium Compounds: A Graphical Review

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-coupling

Biographical Sketches

Balati Hasimujiang was born in Xinjiang Province, P. R. of China. He earned his B.S. in 2011 and his M.S. in 2018, both from Xinjiang Normal University in 2011. In 2020, he joined the group of Prof. Ruan at the School of Pharmaceutical Sciences, Guangzhou Medical University, where he performed his graduate studies and obtained his Ph.D. in June 2023. He is currently undertaking postdoctoral research in the laboratory of Prof. Ruan. His research interests focus on new methodologies in electrochemical synthesis, selenium chemistry, and the synthesis of biologically active compounds.

Zhixiong Ruan was born in Guangdong, P. R. of China. After obtaining his B.Eng. in pharmaceutical engineering at Guangdong University of Technology and his M.Sc. in medicinal chemistry at Jinan University, he joined the research group of Prof. Dr Lutz Ackermann at Georg-August-Universität Göttingen, and obtained his Ph.D. in chemistry in 2017. He was subsequently employed as a professor at the School of Pharmaceutical Sciences, Guangzhou Medical University. His current research interests are focused on organic electrochemistry, peptide modification and synthetic medicinal chemistry.

Organoselenium chemistry has remained a field of persistent exploration ever since selenium was recognized as an essential trace element within the human body. The significance of organoselenium compounds has experienced a substantial surge, particularly since the 1970s, marked by the discovery of numerous intriguing compounds boasting diverse applications in synthesis and biology. Notably, among these compounds, diselenides have emerged as immensely valuable organic entities. The presence of Se–Se bonds confers their distinctive chemical attributes, enabling their involvement in a range of reactions as electrophilic (RSe⁺), nucleophilic (RSe^–), or free-radical (RSe^•) agents.

Over the past decades, advancements have propelled the synthesis of organoselenium molecules, a field often characterized by the routine utilization of costly catalysts and a variety of transition metals. This has spurred an ongoing quest to unearth more economical and environmentally friendly methodologies for generating selenium-containing compounds. Notably, recent breakthroughs in this pursuit have culminated in the development of an efficient and ecologically sound electrochemical selenylation process.

Electrochemistry has become an important strategy in organic synthesis, leading to the development of a multitude of beneficial transformations. One of its strengths lies in its capacity to induce carbon–carbon and carbon–heteroatom bond formation through anodic oxidation, all within an environment free from external oxidants. Notably, the domain of electrochemical synthesis has witnessed a surge in its utilization within the context of the formation of organoselenium compounds. Within the scope of this graphical review, our aim is to provide readers with an extended collection of instances exemplifying the utilization of electrochemical techniques in the synthesis of organoselenium compounds.

Figure 1 Electrochemical C–H selenylation (part 1)[1`] [b] [c] [d] [e] [f] [g] [h] [i] [j] [k] [l]

Figure 2 Electrochemical C–H selenylation (part 2)[1`] [n] [o] [p]

Figure 3 Electrochemical difunctionalization[2`] [b] [c] [d] [e] [f] [g] [h] [i] [j]

Figure 4 Electrochemical selenylation/cyclization (part 1)[3`] [b] [c] [d] [e] [f] [g] [h] [i]

Figure 5 Electrochemical selenylation/cyclization (part 2)[2b] ^, [3`] [k] [l] [m] [n] [o] [p] [q] [r] [s]

Figure 6 Electrochemical selenylation/cyclization (part 3)[2f] ^, [3`] [u] [v] [w] [x] [y] [z]

Figure 7 Electrochemical cross-coupling reactions[4`] [b] [c] [d] [e]

Conflict of Interest

The authors declare no conflict of interest.

Acknowledgment

We are grateful to the current and former members of the Ruan research group who have contributed to the development of this field.

• 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

Publikationsverlauf

Eingereicht: 17. August 2023

Angenommen nach Revision: 21. September 2023

Accepted Manuscript online:
02. Oktober 2023

Artikel online veröffentlicht:
24. Oktober 2023