有机化学 ›› 2023, Vol. 43 ›› Issue (3): 1146-1156.DOI: 10.6023/cjoc202210031 上一篇    下一篇

所属专题: 有机氟化学虚拟合辑 中国女科学家专辑

研究论文

二氟卡宾参与下从邻乙烯基苯胺出发构建3-取代吲哚酮类化合物

黄华a, 李鑫a, 苏建科a, 宋秋玲a,b,c,*()   

  1. a 华侨大学材料科学工程学院 下一代物质转化研究所 福建厦门 361021
    b 中国科学院上海有机化学研究所 金属有机化学国家重点实验室和有机氟化学重点实验室 上海 200032
    c 河南师范大学化学化工学院 河南新乡 453007
  • 收稿日期:2022-10-26 修回日期:2022-11-30 发布日期:2022-12-21
  • 通讯作者: 宋秋玲
  • 基金资助:
    国家自然科学基金(21931013)

Difluorocarbene-Enabled Synthesis of 3-Substituted-2-oxoindoles from o-Vinylanilines

Hua Huanga, Xin Lia, Jianke Sua, Qiuling Songa,b,c()   

  1. a Institute of Next Generation Matter Transformation, College of Material Sciences Engineering, Huaqiao University, Xiamen, Fujian 361021
    b State Key Laboratory of Organometallic Chemistry and Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
    c School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007
  • Received:2022-10-26 Revised:2022-11-30 Published:2022-12-21
  • Contact: Qiuling Song
  • Supported by:
    National Natural Science Foundation(21931013)

开发了一种新型的无需过渡金属参与的合成1-烷基-3-(2-氧代-2-芳基/烷基-乙基)吲哚酮的方法. 这项工作揭示了氧吲哚骨架可以直接由邻乙烯基苯胺和市售的卤代二氟烷基试剂通过C—N裂解/新C—N键和C—C键形成来构建. 该反应具有高效和优异的官能团兼容性, 在药物分子和天然产物的后期修饰中具有巨大潜力.

关键词: 卤代二氟试剂, 3-取代吲哚酮, 二氟卡宾

A novel transition-metal-free protocol for the synthesis of 1-alkyl-3-(2-oxo-2-aryl/alkyl-ethyl)indolin-2-ones is developed. This work reveals that oxoindole skeletons can be directly constructed from ortho-vinylanilines and commercially available halogenated difluoroalkyl reagents via a C—N cleavage/new C—N bonds and C—C bond formation cascade. This reaction portrays high efficiency and excellent functional group compatibility, and has great potential in the late-stage modifications of pharmaceutical molecules and natural products.

Key words: halo difluoro reagent, 3-substituted 2-oxindole, difluorocarbene