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研究论文

钌(Ⅱ)催化吲哚啉与偕-二氟烯烃的C7-H键单氟烯化反应

柏乐乐†,a, 吴庆荣†,a, 李子娟a, 刘兴旺a, 邓璐a, 沈秋娜a, 吴高荣*,a   

  1. (a赣南医科大学药学院, 赣州 341000)
    (b赣州市第五人民医院药剂科,赣州肝病研究所 赣州 341000)
  • 收稿日期:2025-10-23 修回日期:2025-11-25
  • 基金资助:
    江西省自然科学基金(No. 20252BAC200240),江西省职业早期青年科技人才培养专项项目(No.20244BCE52224)和赣南医科大学高层次人才启动基金(No.QD202406)资助项目.

Ruthenium(II)-catalyzed C7-H monofluoroalkenylation of indolines with gem-difluorostyrenes

Bai Lele, Wu Qingrong, Li Zijuana, Liu Xingwanga, Deng Lua, Shen Qiunaa, Wu Gaorong*,a   

  1. (aSchool of Pharmacy, Gannan Medical University, Ganzhou, 341000)
    (bDepartment of Pharmacy, Ganzhou Liver Institute, Ganzhou Fifth People’s Hospital, Ganzhou 341000)
  • Received:2025-10-23 Revised:2025-11-25
  • Contact: *E-mail: gaorongwu09@163.com
  • About author:†These authors contributed equally to this work
  • Supported by:
    Project supported by Jiangxi Provincial Natural Science Foundation (No.20252BAC200240), Early-Career Young Scientists and Technologists Project of Jiangxi Province (No.20244BCE52224) and the Start-up Funds of Gannan Medical University (No.QD202406).

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补充材料

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吲哚啉骨架广泛存在于天然产物、药物和生物活性分子中,将单氟烯烃引入到吲哚啉中有望开发具有药用价值的产品。然而,目前该类研究仅限于通过过渡金属催化,将单氟烯烃引入到吲哚化合物的高活性C2位上,而低活性的C7位单氟烯基化反应却未见报道。通过对吲哚啉进行C7-H键官能化/氧化是获得C7官能化吲哚的有效策略。基于此,本文开发了一种钌(Ⅱ)催化吲哚啉与偕-二氟烯烃的C7-H键单氟烯化反应新方法。该方法展现了良好的官能团容忍性、优异的构型专一性和位点选择性。此外,改方法可进行克级放大,且能通过氧化高效获得吲哚衍生物,为该类结构提供了一种潜在的合成路径。

关键词: 钌(Ⅱ)催化, 吲哚啉, 偕-二氟烯烃, C7-H键单氟烯化, 构型专一性

The indoline skeleton is widely present in natural products, drugs and bioactive molecules. Introducing monofluoroalkenes into indoline is expected to develop products with medicinal value. However, the current research is only limited to the introduction of monofluoroalkenes to the highly reactive C2 position of indole compounds through transition-metal-catalyzed, and the monofluoroalkenylation at the less reactive C7 position has not been reported. Functionalization/oxidation of the C7-H bond of indolines is an effective strategy for obtaining C7-functionalized indoles. Based on this, a novel ruthenium(II)-catalyzed C7-H monofluoroalkenylation of indolines with gem-difluorostyrenes was developed. The protocol exhibited good functional group tolerance, excellent configuration exclusivity and site selectivity. In addition, the method was scale-up implementability and could efficiently obtain indole derivatives through oxidation, which offers a potential synthetic route for this structure.

Key words: ruthenium(II)-catalyzed, indolines, gem-difluorostyrenes, C7-H monofluoroalkenylation, configuration exclusivity