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DOI: https://doi.org/10.6023/cjoc202604031

研究论文

光氧化还原/钯协同催化未活化烯烃氟烷基氟磺酰化合成脂肪族磺酰氟

  • 彭莹莹 ,
  • 张超艺 ,
  • 伍雄 ,
  • 刘忍 ,
  • 庞婉 ,
  • 马晓玉 ,
  • 刘超
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  • 上海应用技术大学化工与能源技术学部,上海绿色氟代制药工程技术研究中心,上海 201418

收稿日期: 2026-04-22

  修回日期: 2026-05-13

  网络出版日期: 2026-06-11

基金资助

国家自然科学基金(No. 22471172)资助项目.

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Aliphatic Sulfonyl Fluoride Synthesis via Fluoroalkylfluorosulfonylation of Unactivated Olefins under Photoredox and Palladium Dual Catalysis

  • Yingying Peng ,
  • Chaoyi Zhang ,
  • Xiong Wu ,
  • Ren Liu ,
  • Wan Pang ,
  • Xiaoyu Ma ,
  • Chao Liu
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  • Faculty of Chemical and Energy Technology and Shanghai Engineering Research Center of Green Fluoropharmaceutical Technology, Shanghai Institute of Technology, Shanghai 201418, People' s Republic of China

Received date: 2026-04-22

  Revised date: 2026-05-13

  Online published: 2026-06-11

Supported by

National Natural Science Foundation of China (No. 22471172).

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摘要

氟烷基和氟磺酰基均为生物活性分子中的重要结构单元,同时也是有机合成中具有重要价值的功能基团。本文报道了一种光氧化还原与钯协同催化的未活化烯烃氟烷基-氟磺酰化反应。该方法以芳基三氟甲基化合物作为氟烷基自由基前体,以1,4-二氮杂双环[2.2.2]辛烷-二氧化硫加合物（DABSO）为二氧化硫来源,N-氟代苯磺酰亚胺（NFSI）为氟源,通过自由基二氧化硫插入氟化（RSIF）策略,实现了碳碳双键的双官能团化转化。在该反应中,氟烷基和氟磺酰基能够一步同时引入到烯烃分子中,从而高效构建结构多样的脂肪族磺酰氟化合物。该反应条件温和,具有良好的官能团兼容性。此外,所得磺酰氟产物可通过SuFEx点击反应进一步转化为多种高附加值化合物。

关键词： 氟烷基氟磺酰化; 磺酰氟; 烯烃双官能团化; 光氧化还原/钯协同催化

本文引用格式

彭莹莹 , 张超艺 , 伍雄 , 刘忍 , 庞婉 , 马晓玉 , 刘超 . 光氧化还原/钯协同催化未活化烯烃氟烷基氟磺酰化合成脂肪族磺酰氟[J]. 有机化学, 0 : 604031 -604031 . DOI: 10.6023/cjoc202604031

Abstract

Both fluoroalkyl and fluorosulfonyl groups are important structural motifs in bioactive molecules and valuable functional units in synthetic chemistry. Herein, we report a photoredox- and palladium-dual-catalyzed fluoroalkylfluorosulfonylation of unactivated olefins using aryl trifluoromethyl compounds as fluoroalkyl radical precursors, 1,4-diazabicyclo[2.2.2]octane-bis(sulfur dioxide) adduct (DABSO) as the sulfur dioxide source, and N-fluorobenzenesulfonimide (NFSI) as the fluorine source via radical sulfur dioxide insertion and fluorination strategy. This transformation enables the simultaneous installation of fluoroalkyl and fluorosulfonyl groups across carbon-carbon double bonds in a single step, thus providing an efficient and concise approach to structurally diverse aliphatic sulfonyl fluorides. The reaction proceeds under mild conditions and exhibits good functional-group tolerance. Furthermore, the resulting sulfonyl fluoride products can be readily transformed into valuable compounds through SuFEx reactions.

Key words： fluoroalkylfluorosulfonylation; sulfonyl fluorides; alkene difunctionalization; photoredox/palladium dual catalysis

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