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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Entry	Variation from the standard reaction conditions	Yield^b/%
1	None	76
2	Ligands other than L6	Trace~69
3	Catalysts other than NiBr₂	21~65
4	Solvents other than DMSO	Trace~73
5	Zn instead of Mn	17
6	Room temperature instead of 60 ℃	N.R.

Entry	Variation from the standard reaction conditions	Yield^b/%
1	None	76
2	Ligands other than L6	Trace~69
3	Catalysts other than NiBr₂	21~65
4	Solvents other than DMSO	Trace~73
5	Zn instead of Mn	17
6	Room temperature instead of 60 ℃	N.R.

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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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