Nickel-Catalyzed Reductive Cascade Arylalkylation of Alkenes with Cyclosulfonium Salts

doi:10.6023/cjoc202507038

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (2): 653-663.DOI: 10.6023/cjoc202507038 Previous Articles Next Articles

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镍催化烯烃与环硫鎓盐的还原串联芳烷基化反应

张云一^a, 严含冰^b, 朱先进^c, 石永佳^a, 李俊鑫^a^,^*(), 杨道山^a^,^*(), 李旭锋^c^,^*()

^a 青岛科技大学化学与分子工程学院山东青岛 266042
^b 东北林业大学奥林学院哈尔滨 150040
^c 浙江万盛股份有限公司浙江临海 317000

收稿日期:2025-07-29 修回日期:2025-09-01 发布日期:2025-10-09
通讯作者: 李俊鑫, 杨道山, 李旭锋
基金资助:
国家自然科学基金(22271170); 山东省青年泰山学者项目(tsqn202408197); 山东省自然科学基金(22271170)

Nickel-Catalyzed Reductive Cascade Arylalkylation of Alkenes with Cyclosulfonium Salts

Yunyi Zhang^a, Hanbing Yan^b, Xianjin Zhu^c, Yongjia Shi^a, Junxin Li^a^,^*(), Daoshan Yang^a^,^*(), Xufeng Li^c^,^*()

^a College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao, Shandong 266042
^b Aulin College, Northeast Forestry University, Harbin 150040
^c Zhejiang Wansheng Co., Ltd., Linhai, Zhejiang 317000

Received:2025-07-29 Revised:2025-09-01 Published:2025-10-09
Contact: Junxin Li, Daoshan Yang, Xufeng Li
Supported by:
National Natural Science Foundation of China(22271170); Taishan Scholars Program from Shandong Province(tsqn202408197); Natural Science Foundation of Shandong Province(22271170)

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Abstract

Nickel-catalyzed reductive cross-coupling (RCC) reactions between alkenes and alkyl electrophiles are undoub- tedly 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. A new nickel- catalyzed reductive arylalkylation of tethered alkenes with cyclosulfonium salts as C(sp³) electrophiles to access the sulfur- containing oxindoles is developed. 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

Yunyi Zhang, Hanbing Yan, Xianjin Zhu, Yongjia Shi, Junxin Li, Daoshan Yang, Xufeng Li. Nickel-Catalyzed Reductive Cascade Arylalkylation of Alkenes with Cyclosulfonium Salts[J]. Chinese Journal of Organic Chemistry, 2026, 46(2): 653-663.

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References 11

[11]	(d) Lv Y.; Cui H.; Meng N.; Yue H.; Wei W. Chin. Chem. Lett. 2022, 33, 97.
	(e) Wang M.; Jiang X. ACS Sustainable Chem. Eng. 2022, 10, 671.
	(f) Peng Q.-H.; Jiang J.; Liao Z.-H.; Wu Z.-L.; Ou L.-J.; Dai H.; Peng J.; He W.-M. ACS Sustainable Chem. Eng. 2025, 13, 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.
	(d) Xu H.; Li X.; Ma J.; Zuo J.; Song X.; Lv J.; Yang D. Chin. Chem. Lett. 2023, 34, 108403.
	(e) Xu H.; Li X.; Wang Y.; Song X.; Shi Y.; Lv J.; Yang D. Org. Lett. 2024, 26, 1845.
	( (f) Xu H.; Zhang J.; Zuo J.; Wang F.; Lv J.; Hun X.; Yang D. Chin. J. Org. Chem. 2022, 42, 4037 (in Chinese).
	( 徐浩, 张杰, 左峻泽, 王丰晓, 吕健, 混旭, 杨道山, 有机化学, 2022, 42, 4037.)
[13]	Ma J.; Li X.; Chen Y.; Shi, Yong, Song X.; Lv J.; Yang D. Chin. J. Chem. 2024, 42, 1637.
[1]	( a) Sui D.; Cen N.; Gong R.; Chen Y.; Chen W. Chin. J. Org. Chem. 2023, 43, 3239 (in Chinese).
	( 岁丹丹, 岑南楠, 龚若蕖, 陈阳, 陈文博, 有机化学, 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.
	( (d) Xin C.; Jiang J.; Deng Z.-W.; Ou L.-J.; He W.-M. Acta Chim. Sinica 2024, 82, 1109 (in Chinese).
	( 辛翠, 蒋俊, 邓紫微, 欧丽娟, 何卫民, 化学学报, 2024, 82, 1109.)
	( (e) Tan Y.; Shu H.; Huang H. Chin. J. Org. Chem. 2025, 45, 2086 (in Chinese).
	( 永波, 舒洪波, 黄华文, 有机化学, 2025, 45, 2086.)
	( (f) Li F.; Lu B.; Liu Y.; Wang X. Chin. J. Org. Chem. 2022, 42, 3390 (in Chinese).
	( 李芳洁, 卢斌, 刘阳, 王晓明, 有机化学, 2022, 42, 3390.)
	( (g) Guo X.; Guo Y.; Kong D.; Lu H.; Hua Y.; Wang M. Chin. J. Org. Chem. 2020, 40, 1999 (in Chinese).
	( 郭欣, 郭亚军, 孔德志, 卢会杰, 华远照, 王敏灿, 有机化学, 2020, 40, 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) Lu Y.-H.; Mu, S-Y.; Jiang J.; Zhou M.-H.; Wu C.; Ji H.-T.; He W.-M. ChemSusChem 2023, 16, e202300523.
	(d) Ouyang W.-T.; Jiang J.; Jiang Y.-F.; Li T.; Liu Y.-Y.; Ji H.-T.; Ou L.-J.; He W.-M. Chin. Chem. Lett. 2024, 35, 110038
[3]	a) Weix D. J. 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.
	( (d) Xie S.; Li W.; Liu Y.; Lu X.; Shi R. Chin. J. Org. Chem. 2025, 45, 2121 (in Chinese).
	( 谢沈彤, 李文静, 刘钰, 陆熹, 师仁义, 有机化学, 2025, 45, 2121.)
	(e) Wu Y.; Chen J.-Y.; Ning J.; Jiang X.; Deng J.; Deng Y.; Xu R.; He W.-M. Green Chem. 2021, 23, 3950.
	(f) Ji H.-T.; Wang K.-L.; Ouyang W.-T.; Luo Q.-X.; Li H.-X.; He W.-M. Green Chem. 2023, 25, 7983.
	( (g) Zhang X.; Lin S.; Huang X. Chin. J. Org. Chem. 2024, 44, 3456 (in Chinese).
	( 张鑫伟, 林水侦, 黄晓雷, 有机化学, 2024, 44, 3456 )
[4]	a) Poremba K. E.; Dibrell S. E.; Reisman S. E. ACS Catal. 2020, 10, 8237.
	(b) Wang K.; Ding Z.; Zhou Z.; Kong W. J. Am. Chem. Soc. 2018, 140, 12364.
[5]	Jin Y.; Yang H.; Wang C. Org. Lett. 2019, 21, 7602.
[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.
[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. Synthesis 2022, 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. 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.

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镍催化烯烃与环硫鎓盐的还原串联芳烷基化反应

Nickel-Catalyzed Reductive Cascade Arylalkylation of Alkenes with Cyclosulfonium Salts

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