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

研究论文

镍催化烯烃与环硫鎓盐的还原串联芳烷基化反应

  • 张云一 ,
  • 严含冰 ,
  • 朱先进 ,
  • 石永佳 ,
  • 李俊鑫 ,
  • 杨道山 ,
  • 李旭锋
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  • a青岛科技大学 化学与分子工程学院 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 临海 317000

收稿日期: 2025-07-29

  修回日期: 2025-09-01

  网络出版日期: 2025-10-10

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项目(22271170)资助.

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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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摘要

镍催化的烯烃与烷基亲电试剂之间的还原交叉偶联反应是构建杂环化合物的重要方法之一。然而,通过还原交叉偶联反应实现烯烃芳烷基化的烷基化试剂仍相当有限。开发以稳定且易得的起始原料通过还原偶联策略合成杂环化合物的更为普适的方法仍具有挑战性且亟待开发。在此,我们发展了一种新的镍催化还原串联芳烷基化反应：以环硫鎓盐作为C(sp³)亲电试剂,通过镍催化的还原偶联策略实现烯烃的芳烷基化,从而合成一系列含硫醚片段的氧化吲哚类化合物。该串联开环/环化/还原偶联策略可在温和条件下高效构建多种带有全碳季碳中心的氧化吲哚,并具有优异的官能团兼容性。值得注意的是,许多药物衍生物均可利用该策略直接实现官能化.

关键词： 镍催化; 还原偶联; 烷基化; C-C键; 串联反应

本文引用格式

张云一 , 严含冰 , 朱先进 , 石永佳 , 李俊鑫 , 杨道山 , 李旭锋 . 镍催化烯烃与环硫鎓盐的还原串联芳烷基化反应[J]. 有机化学, 0 : 202507038 -202507038 . DOI: 10.6023/cjoc202507038

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

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