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有机化学
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有机化学 ›› 2026, Vol. 46 ›› Issue (7): 2789-2795.DOI: 10.6023/cjoc202602003 上一篇    下一篇

研究论文

无配体铜催化四氢-β-咔啉的氧化重排反应

李凌岳†, 张嘉沛†, 张硕, 崔露元, 刘希功*(), 刘磊   

  1. 山东大学化学与化工学院 济南 250100
  • 收稿日期:2026-02-02 修回日期:2026-03-21 发布日期:2026-05-13
  • 作者简介:

    †共同第一作者

  • 基金资助:
    国家自然科学基金(22571185); 国家自然科学基金(22425108); 国家重点研发计划(2024YFA1509204); 国家重点研发计划(2024YFA1509202); 山东省泰山学者计划和山东省自然科学基金(ZR2025MS252)

Ligand-Free Copper-Catalyzed Oxidative Rearrangement of Tetrahydro-β-carbolines

Lingyue Li†, Jiapei Zhang†, Shuo Zhang, Luyuan Cui, Xigong Liu*(), Lei Liu   

  1. School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100
  • Received:2026-02-02 Revised:2026-03-21 Published:2026-05-13
  • Contact: *E-mail: xigongliu@sdu.edu.cn
  • About author:

    †(These authors contributed equally to this work).

  • Supported by:
    National Natural Science Foundation of China(22571185); National Natural Science Foundation of China(22425108); National Basic Research Program of China(2024YFA1509204); National Basic Research Program of China(2024YFA1509202); Taishan Scholar Program at Shandong Province, the Natural Science Foundation of Shandong Province(ZR2025MS252)

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螺氧化吲哚作为一类基本骨架, 广泛存在于多种天然产物及生物活性分子中. 吲哚的氧化重排反应已成为构建该类螺环结构最高效的策略之一. 报道了一例无配体参与铜催化的吲哚的氧化重排反应. 在温和的反应条件下, 该方法能够以90%~96%的收率得到结构多样的螺氧化吲哚化合物. 此外, 该方法还具有优异的官能团耐受性和底物适用范围, 无配体参与的反应条件也提高了其在合成化学中的应用价值.

关键词: 无配体, 丰产金属催化, 铜催化, 螺氧化吲哚, 氧化重排

The oxidative rearrangement of indoles has emerged as a prominent and highly efficient strategy for accessing spirooxindoles, a privileged scaffold prevalent among bioactive molecules and natural products. Herein, a ligand-free copper-catalyzed oxidative rearrangement of indoles is reported, and structurally diverse spirooxindoles were obtained in 90%~96% yields under mild reaction conditions. The reaction exhibits excellent functional group tolerance and a broad substrate scope, with the ligand-free conditions significantly enhancing its synthetic utility.

Key words: ligand-free, earth-abundant metal catalysis, copper-catalysis, spirooxindole, oxidative rearrangement