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Chinese Journal of Organic Chemistry >

0 202507038 - 202507038

DOI: https://doi.org/10.6023/cjoc202507038

ARTICLE

Nickel-catalyzed reductive cascade arylalkylation of alkenes with cyclosulfonium salts

  • Zhang Yunyi ,
  • Yan Hanbing ,
  • Zhu Xianjin ,
  • Shi Yongjia ,
  • Li Junxin ,
  • Yang Daoshan ,
  • Li Xufeng
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  • aCollege of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao, 266042,China;
    bAulin College, Northeast Forestry University, Harbin 150040, China;
    cZhejiang Wansheng Co., Ltd., Linhai, Zhejiang 317000, China

Received date: 2025-07-29

  Revised date: 2025-09-01

  Online published: 2025-10-10

Supported by

National Natural Science Foundation of China (22271170), the Taishan Scholars Program from Shandong Province (tsqn202408197), the Natural Science Foundation of Shandong Province (ZR2024QB154).

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Abstract

Nickel-catalyzed reductive cross-coupling (RCC) reactions between alkenes and alkyl electrophiles are undoubtedly the attractive approaches to new functionalized heterocycles. However, the alkylation reagents are still rather limited for the arylalkylation of tethered alkenes via RCC reactions. Thus, developing more robust methods to access heterocycles from stable and readily available starting materials under RCC conditions is still highly challenging and desirable. We show here, a new nickel-catalyzed reductive arylalkylation of tethered alkenes with cyclosulfonium salts as C(sp3) electrophiles to access the sulfur-containing oxindoles. This tandem ring-opening/cyclization/reductive coupling protocol enables the efficient construction of various oxindoles bearing all-carbon quaternary centers under mild conditions with broad functional group tolerance. Notably, many drug derivatives are readily functionalized using the developed protocol.

Key words： nickel catalysis; reductive coupling; alkylation; C-C bond; cascade reaction

Cite this article

Zhang Yunyi , Yan Hanbing , Zhu Xianjin , Shi Yongjia , Li Junxin , Yang Daoshan , Li Xufeng . Nickel-catalyzed reductive cascade arylalkylation of alkenes with cyclosulfonium salts[J]. Chinese Journal of Organic Chemistry, 0 : 202507038 -202507038 . DOI: 10.6023/cjoc202507038

References

[1] (a) Sui, D.; Cen, N.; Gong, R.; Chen, Y.; Chen, W.Chin. J. Org. Chem. 2023, 43, 3239.
(b) Hou, J.-C.; Jiang, J.; Dai, H.; Wang, J.-S.; Li, T.; Chen, X.; He, W.-M.,Sci. China Chem. 2025, 68, 1945.
(c) Lu, Y.-H.; Zhang, Z.-T.; Wu, H.-Y.; Zhou, M.-H.; Song, H.-Y.; Ji, H.-T.; Jiang, J.; Chen, J.-Y.; He, W.-M., Chin. Chem. Lett. 2023, 34, 108036., 1999.
[2] (a) Cao Z.-Y.; Zhou F.; Zhou, J. Acc. Chem. Res.2018, 51, 1443.
(b) Gui Q.-W.; Teng F.; Li Z.-C.; Xiong Z.-Y.; Jin X.-F.; Lin Y.-W.; Cao Z.; He, W.-M. Chin. Chem. Lett.2021, 32, 1907.
(c) Pan, Q.; Ping, Y.; Kong, W. Acc. Chem. Res. 2023, 56, 515., 110038
[3] (a) Weix, D. J. Methods. Acc. Chem. Res.2015, 48, 1767.
(b) Ping Y.; Li Y.; Zhu J.; Kong, W. Angew. Chem. Int. Ed.2019, 58, 1562.
(c) Xi, L.; Du, L.; Shi, Z. Chin. Chem. Lett. 2022, 33, 4287., 3456.
[4] (a) Pan Q.; Ping Y.; Kong, W. Acc. Chem. Res.2023, 56, 515.
(b) Poremba, K. E.; Dibrell, S. E.; Reisman, S. E. ACS Catal. 2020, 10, 8237.
(c) Wang K.; Ding Z.; Zhou Z.; Kong, W. Ni-Catalyzed Enantioselective Reductive Diarylation of Activated Alkenes by Domino Cyclization/Cross-Coupling. J. Am. Chem. Soc.2018, 140, 12364.
[5] Jin Y.; Yang H.; Wang, C. Nickel-Catalyzed Reductive Arylalkylation via a Migratory Insertion/Decarboxylative Cross-Coupling Cascade. Org. Lett.2019, 21, 7602-7608.
[6] (a) Jin Y.; Wang, C. Angew. Chem. Int. Ed.2019, 58, 6722.
(b) Pan Q.; Wang K.; Xu W.; Ai Y.; Ping Y.; Liu C.; Wang M.; Zhang J.; Kong, W. J. Am. Chem. Soc. 2024, 146, 15453.
(c) Fang K.; Huang W.; Shan C.; Qu Ji.; Chen Y. Org. Lett.2021, 23, 5523-5527.
[7] (a) Yang J.; Yang L.; Gu J.; Shuai L.; Wang H.; Ouyang Q.; Li Y.-L.; Liu H.; Gong L. Org. Lett.2022, 24, 2376.
(b) Pan, Q.; Ping, Y.; Kong, W.Acc. Chem. Res. 2023, 56, 515.
[8] (a) Tian Z.-Y.; Ma Y.; Zhang C.-P. Synthesis2022, 54, 1478.
(b) Kozhushkov S. I.; Alcarazo, M. Eur. J. Inorg. Chem.2020, 2020, 2486.
(c) Fan, R.; Tan, C.; Liu, Y.; Wei, Y.; Zhao, X.; Liu, X.; Tan, J. Chin. Chem. Lett. 2021, 32, 299.
[9] (a) Berger, F.; Plutschack, M. B.; Riegger, J.; Yu, W.; Speicher, S.; Ho, M.; Frank, N.; Ritter, T. Site-selective and versatile aromatic C-H functionalization by thianthrenation. Nature 2019, 567, 223.
(b) Zhang, M.; Liu, L.; Wang, B.; Yang, Y.; Liu, Y.; Wang, Z.; Wang, Q ACS Catal. 2023, 13, 11580.
(c) Meng, H.; Liu, M.-S.; Shu, W. Chem. Sci. 2022, 13, 13690.
(d) Song, H.-Y.; Jiang, J.; Wu, C.; Hou, J.-C.; Lu, Y.-H.; Wang, K.-L.; Yang, T.-B.; He, W.-M., Green Chem. 2023, 25, 3292.
(e) Wu, J.; Wang, Z.; Chen, X.-Y.; Wu, Y.; Wang, D.; Peng, Q.; Wang, P. Sci. China Chem. 2020, 63, 336.
[10] Lansbergen B.; Granatino P.; Ritter, T. J. Am. Chem. Soc.2021, 143, 7909.
[11] (a) Lou J.; Wang Q.; Wu P.; Wang H.; Zhou Y.-G.; Yu, Z. Chem. Soc. Rev.2020, 49, 4307.
(b) Yang D.; Yan Q.; Zhu E.; Lv J.; He, W.-M. Chin. Chem. Lett.2022, 33, 1798.
(c) Liu, C.-H.; Zhang, Z.-W.; Zhao, Z.-J.; Jiang, J.; Yang, Z.; Wang, Z.-L.; He, W.-M., J. Org. Chem. 2025, 90, 11982., 10971.
[12] (a) Yan Q.; Cui W.; Song X.; Xu G.; Jiang M.; Sun K.; Lv J.; Yang D. Org. Lett.2021, 23, 3663.
(b) Zhu X.; Jiang M.; Li X.; Zhu E.; Deng Q.; Song X.; Lv J.; Yang, D. Org. Chem. Front.2022, 9, 347.
(c) Li, X.; Cui, W.; Deng, Q.; Song, X.; Lv, J.; Yang, D. Green Chem. 2022, 24, 1302., 4037
[13] Ma J.; Li X.; Chen Y.; Shi, Yong, Song X.; Lv J.; Yang, D. Chin. J. Chem.2024, 42, 1637.
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