ARTICLE

Electrochemical Sulfonylation of Alkenes and Sulfonyl Hydrazides under Metal-Free Conditions

  • Xue Jian ,
  • Wang Kun ,
  • Zhang Hao ,
  • Xue Jiale ,
  • Deng Yaqi
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  • College of Chemistry and Materials Science, Weinan Normal University, Shaanxi 714099

Received date: 2026-04-14

  Revised date: 2026-06-14

  Online published: 2026-09-08

Supported by

Discipline Construction Project of Weinan Normal University (No. 2025XKJS03).

Abstract

We report an environmentally friendly and highly efficient electrochemical protocol for the synthesis of vinyl sulfones. This method enables the direct coupling of readily available sulfonyl hydrazides with alkenes under mild, metal-free, exogenous oxidant-free and iodide-additive-free conditions, delivering the corresponding vinyl sulfones in excellent yields. The protocol features broad substrate scope, good functional group tolerance and is amenable to gram-scale synthesis. Moreover, the prepared vinyl sulfone derivatives exhibit excellent anti-proliferative activity against osteosarcoma cell lines. This work provides a practical and sustainable alternative for the green synthesis and medicinal research of valuable vinyl sulfone compounds.

Cite this article

Xue Jian , Wang Kun , Zhang Hao , Xue Jiale , Deng Yaqi . Electrochemical Sulfonylation of Alkenes and Sulfonyl Hydrazides under Metal-Free Conditions[J]. Chinese Journal of Organic Chemistry, 2026 : 202604021 . DOI: 10.6023/cjoc202604021

References

[1] (a) Zhu Q.; Cheng L.; Lu Y. Chem. Commun.2008, 12, 6315.
(b) Zhao P.; Beaudry, C. M. Angew. Chem., Int. Ed.2014, 53, 9944.
[2] Li Y.-M.; Liu Y.; Ngai M.-Y.; Hong X.; Wu, Y.-D. J. Am. Chem. Soc.2019, 141, 7267.
[3] (a) Wang, G.; Mahesh, U.; Chen, Y.-J.; Yao, S.-Q. Org. Lett. 2003, 5, 737.
(b) Uttamchandani, M.; Liu, K.; Panicker R.-C.; Yao, S.-Q. Chem. Commun. 2007, 15, 18.
(c) Sebti, S.-A.; Hamilton, R.-J. Cancer Res. 2009, 69, 7602.
(d) Das, A.-K.; Islam. M.-R. J. Nat. Prod. 2018, 81, 2323.
(e) Raju, S.-R.; Niyomrattanakit. S.-K. J. Med. Chem. 2024, 67, 1346.
[4] Merten E.-M.; Sears J.-D.; Leisner T.-M.; Hardy P.-B.; Ghoshal A.; Hossain M.-A.; Asressu K.-H.; Brown P.-J.; Stashko M.-A.; Herring L.-E. bioRxiv. 2024, 22, 586341.
[5] McKerrow, J.-H. PLoS Negl Trop Dis.2018, 12, e0005850.
[6] Lu T.-G.; Laughton C.-A.; Wang S.-D.; Tracey D.-B. Mol. Pharmacol.2015, 87,18.
[7] (a) Li, X.; Xu, X.; Zhou, C. Chem. Commun. 2012, 48, 12240.
(b) Tang, S.; Wu, Y.; Liao, W.-Q.; Bai, R.-P.; Liu C.; Lei, A.-W. Chem. Commun. 2014, 50, 4496.
(c) Xu, Y.; Tang, X.; Hu, W.; Jiang, H. Green Chem. 2014, 16, 3720.
(d) Singh, R.; Allam, B. K.; Singh, N.; Kumari, K.; Singh S. K.; Singh, K. N. Org. Lett. 2015, 17, 2656.
(e) Yue, H.; Zhu, C.; Rueping, M. Angew. Chem., Int. Ed. 2018, 57, 1371.
(f) Zhang, G.; Fu, J.-G.; Zhao, Q.; Zhang, G.-S.; Li, M.-Y.; Feng, C.-G.; Lin, G.-Q. Chem. Commun. 2020, 56, 4688.
[8] (a) Chodroff S.; Whitmore, W.-F. J. Am. Chem. Soc.1950, 72, 1073.
(b) Balasubramanian M.; Baliah, V. J. Am. Chem. Soc.1954, 12, 1844.
(c) Happer, D. A.; Steenson, B. E. synth. 1980, 10, 806.
[9] (a) Hopkins P. B.; Fuchs, P. L. J. Org. Chem.,1978, 43, 1208.
(b) Gancarz R.-A.; Kice J.-L. Tetrahedron Lett.1980, 21, 4155.
[10] (a) Huang, X.; Duan, D. H.; Zheng, X.J. Org. Chem., 2003, 68, 1958.
(b) Kirihara M.; Yamamoto J.; Noguchi T.; Hirai Y. Tetrahedron Lett.2009, 50, 1180.
[11] (a) Reeves D.-C.; Rodriguez S.; Lee H.; Haddad N.; Krishnamurthy D.; Senanayake, C. H. Tetrahedron Lett.2009, 50, 2870.
(b) Jiang H.; Chen X.; Zhang Y.; Yu, S. Adv. Synth. Catal.2013, 355, 809.
[12] (a) Singh R.; Allam B.-K.; Singh N.; Kumari K.; Singh S.-K.; Singh K.-N. Org. Lett.2015, 17, 2656.
(b) Chen J.; Mao J.; Zheng Y.; Liu D.; Rong G.; Yan H.; Zhang C.; Shi D. Tetrahedron.2015, 71, 5059.
(c) Cao, K.; Zhang, N.-Y.; Lin, L.; Shen, Q.; Jiang, H.-Z.; Li, J.-H. Adv. Synth. Catal. 2024, 336, 207.
[13] (a) Qian P.; Bi M.; Su J.; Zha Z.; Wang, Z. J. Org. Chem.2016, 81, 4876.
(b) Liu X.; Zhang Y.; Zheng Y.; Huang C.-F.; Cao, H. Chin. J. Chem.2024, 42, 1367.
(c) Wang, X.-M.; Chen, Q.-Q.; Zhou, J.-H.; Hu, Y.; Ye, S.-Q.; Wu, J. Chin. J. Chem. 2025, 43, 292.
[14] (a) Yang, Z.-X.; Ding, L.-C.; Yang, G.-H.; Wang, D.-Y.; Shi, L.; Li, Y.-N.; Liang, D.-Q. J. Org. Chem. 2024, 89, 10660.
(b) Peng, X.; Tao, S.-K.; Xue, W.-C.; Fu, H.-Y.; Xu, J.-Q.; Li, R.-X.; Chen, H.; Zheng, X.-L. Org. Lett. 2024, 26, 4018.
(c) Zhao, Z.-H.; Yan, H.-Y.; Zhou,Y.-Q.; Xue, W.; Gu, L.-J.; Zhang, S.-Y. Chin. J. Chem. 2024, 42, 2049.
(d) Zhang, X.; Li, W.; Zhou, Y.-X.; Lv, S.-H.; Xu, L.-C.; Shi, L.; Li, Y.-N.; Liang, D.-Q. Org. Chem. Front. 2024, 11, 5564.
(e) He, T.-Y.; Xiang, F.-R.; Duan, Y.; Liu, Q.; Zheng, Y.; Zhang, X.-X.; Wang, M.-Y.; Huang, S.-L. Org. Lett. 2025, 27, 8099.
(f) Zhao, Z.-H.; Yan, H.-Y.; Gu, L.-J. Chem. Commun. 2025, 61, 3868.
(g) Liu, B.-C.;Liang, H.; Lu, Y.-J.; Huang, S.-L. Org. Lett. 2025, 27, 2170.
[15] (a) Wang, H.-Y.; Chen, X.-L.; Wu, Y.-D.; Wu, A.-X. Chin. J. Chem. 2023, 41, 3388.
(b) Wu, L.-J.; Zhang, K.-Y.; Yang, P.; Peng, C.-C.; Liu, J.-H.; Li, Q.; Sun, D.-Z.; Yin, S.-F. Chin. J. Chem. 2024, 42, 1853.
(c) Ma, Y.-C.; Yu, M.-P.; Qin, R.-Y.; He, R.; Zeng, L.; Shi, L.; Sun, S.-G.; Liang, D.-Q. J. Org. Chem. 2025, 90, 598.
(d) Ding, L.-C.; Yang, G.-H. Luo, L.; Ma, Y.-C.; Shi, J.-F.; Liang, D.-Q.; Li, Y.-N. Chin. J. Chem. 2025, 43, 491.
[16] Lai Y.-L.; Mo Y.-Y.; Yan S.-X.; Zhang, S.-L,; Zhu L.-J.; Luo J.-M.; Guo H.-S.; Cai J.-P.; Liao J.-H. RSC Adv.2020, 10, 33155.
[17] Alexander O.; Terent'ev O.; Mulina M.; Dmitry A.; Pirgach A.-I.; Mikhail A.; Nadezhda I.; Gennady I. Tetrahedron.2017, 7, 6871.
[18] Yuan Y.; Cao Y.-M.; Lin Y.-P.; Li Y.-L.; Huang Z.-L.; Lei A.-W. ACS Catal.2018, 8, 10871.
[19] Xue J.; Li M.; Wang Y.; Sun D.-H.; Hao S.-L.; Liu, S. Y. Eur. J. Med. Chem.2026, 302, 118355.
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