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DOI: https://doi.org/10.6023/cjoc202604016

研究论文

铜催化非张力环烷基硅基过氧化物的开环氟磺酰化反应

  • 马余学 ,
  • 裴妮萍 ,
  • 李彦辉 ,
  • 李玮 ,
  • 王力竞
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  • a河北大学化学与材料科学学院 保定 071002;
    b药物化学与分子诊断教育部重点实验室 河北省化学生物学重点实验室 保定 071002

收稿日期: 2026-04-08

  修回日期: 2026-05-20

  网络出版日期: 2026-08-17

基金资助

河北省自然科学基金面上项目(No. B2025201101),河北省创新能力提升计划项目(No. 22567632H),河北大学实验室开放项目(No. sy202533)资助.

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Copper-Catalyzed Ring-Opening Fluorosulfonylation of Unstrained cyclic Alkylsilyl Peroxides

  • Ma Yuxue ,
  • Pei Niping ,
  • Li Yanhui ,
  • Li Wei ,
  • Wang Lijing
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  • aCollege of Chemistry and Materials Science, Hebei University, Baoding City, 071002;
    bKey Laboratory of Medicinal Chemistry and Molecular Diagnosis of the Ministry of Education, Key Laboratory of Chemical Biology of Hebei Province, Baoding, 071002

Received date: 2026-04-08

  Revised date: 2026-05-20

  Online published: 2026-08-17

Supported by

Natural Science Foundation of Hebei Province (No. B2025201101), the Hebei Province Innovation Capability Enhancement Plan Project (No. 22567632H), and the Hebei University Laboratory Open Project (No. sy202533) for financial support.

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摘要

磺酰氟化合物（R-SO2F）凭借其稳定性与独特的反应活性,已经成为有机合成、药物研发与材料科学等领域的重要分子。本文报道了一种在铜催化条件下,促使非张力环烷基硅基过氧化物开环,之后通过含远端羰基烷基自由基的二氧化硫插入/氟化策略,合成相应脂肪族磺酰氟化合物的新方法。该方法操作简便,条件温和,可适用于多元环骨架及带有不同取代基的底物,且所得产物能够顺利进行多种后续SuFEx衍生化反应。为合成新型烷基磺酰氟化合物提供了新思路。

关键词： 铜催化; 磺酰氟; 非张力环开环; 二氧化硫插入; SuFEx反应

本文引用格式

马余学 , 裴妮萍 , 李彦辉 , 李玮 , 王力竞 . 铜催化非张力环烷基硅基过氧化物的开环氟磺酰化反应[J]. 有机化学, 0 : 202604016 . DOI: 10.6023/cjoc202604016

Abstract

Sulfonyl fluorides (R‑SO2F) have emerged as versatile building blocks in organic synthesis, medicinal chemistry, and materials science, owing to their excellent stability and unique reactivity. Herein, we report a concise copper-catalyzed protocol for the synthesis of carbonyl-containing aliphatic sulfonyl fluorides from unstrained cycloalkyl silyl peroxides, involving sequential ring-opening, SO₂ insertion, and fluorination of alkyl radicals. This approach features mild conditions, operational simplicity, and broad substrate scope, tolerating various cyclic skeletons and functional groups. Furthermore, the products readily undergo diverse downstream SuFEx derivatizations, providing a new strategy for the assembly of structurally diverse alkyl sulfonyl fluorides.

Key words： copper catalysis; sulfonyl fluoride; unstrained ring opening; sulfur dioxide insertion; SuFEx reaction

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