钯催化非活化烯烃的分子内Heck/胺化反应合成螺吲哚啉

doi:10.6023/cjoc202604014

有机化学

研究论文

钯催化非活化烯烃的分子内Heck/胺化反应合成螺吲哚啉

林艳如^a,b, 周倩^b, 秦景灏^b, 宋德威^b, 宋芳芳^b, 高媛媛^b, 包欢^a, 李飞^a,*, 姜恒^a,*, 刘澜涛^b,*

^a辽宁石油化工大学石油化工学院辽宁抚顺 113001;
^b商丘师范学院化学化工学院河南省药物绿色合成工程研究中心河南商丘 476000

收稿日期:2026-04-07 修回日期:2026-05-17
基金资助:
河南省自然科学基金（Nos. 262300421296, 252300423729）资助项目.

Palladium-Catalyzed Intramolecular Heck/Amination of Unactivated Alkenes for the Synthesis of Spiroindolines

Lin Yan-Ru^a,b, Zhou Qian^b, Qin Jinghao^b, Song Dewei^b, Song Fang-Fang^b, Gao Yuan-Yuan^b, Bao Huan^a, Li Fei^a,*, Jiang Heng^a,*, Liu Lantao^b,*

^aSchool of Petrochemical Engineering, Liaoning Petrochemical University, Fushun, Liaoning 113001;
^bHenan Engineering Laboratory of Green Synthesis for Pharmaceuticals, School of Chemistry and Chemical Engineering, Shangqiu Normal University, Shangqiu, Henan 476000

Received:2026-04-07 Revised:2026-05-17
Contact: ^*E-mail: lnpulf@126.com; hjiang78@hotmail.com; liult05@iccas.ac.cn.
Supported by:
Natural Science Foundation of Henan (Nos. 262300421296 and 252300423729)

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摘要/Abstract

螺吲哚啉广泛存在于天然生物碱和生物活性化合物中。本文通过钯催化的非活化烯烃分子内Heck/胺化反应,构建了一系列螺吲哚啉骨架。该反应利用分子内固有的N-H部分作为亲核试剂,无需外加亲核试剂,以良好至中等的收率获得了目标产物。此外,我们还对该反应的不对称版本进行了初步尝试,最高以85%的收率和65%的ee值获得了具有光学活性的螺吲哚啉。该工作为螺吲哚啉的合成提供了一种新颖、简便的方法,具有潜在的药物化学应用价值。

关键词: 螺吲哚啉, 钯催化, Heck/胺化反应, 分子内环化

Spiroindolines are widely present in natural alkaloids and biologically active compounds. Herein, a palladium-catalyzed intramolecular Heck/amination of unactivated alkenes was developed to construct a series of spiroindoline frameworks. The reaction employs the intrinsic intramolecular N-H moiety as the sole nucleophile, affording the desired products in good to moderate yields. In addition, preliminary attempts toward an asymmetric version of this reaction have also been conducted, providing optically active spiroindolines in up to 85% yield and 65% ee. This work provides a novel and straightforward approach for the synthesis of spiroindolines with potential applications in medicinal chemistry.

Key words: Spiroindolines, Palladium-Catalyzed, Heck/Amination Reaction, Intramolecular Cyclization

引用此文

林艳如, 周倩, 秦景灏, 宋德威, 宋芳芳, 高媛媛, 包欢, 李飞, 姜恒, 刘澜涛. 钯催化非活化烯烃的分子内Heck/胺化反应合成螺吲哚啉[J]. 有机化学, doi: 10.6023/cjoc202604014.

Lin Yan-Ru, Zhou Qian, Qin Jinghao, Song Dewei, Song Fang-Fang, Gao Yuan-Yuan, Bao Huan, Li Fei, Jiang Heng, Liu Lantao. Palladium-Catalyzed Intramolecular Heck/Amination of Unactivated Alkenes for the Synthesis of Spiroindolines[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202604014.

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钯催化非活化烯烃的分子内Heck/胺化反应合成螺吲哚啉

Palladium-Catalyzed Intramolecular Heck/Amination of Unactivated Alkenes for the Synthesis of Spiroindolines

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