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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*   

  1. 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
  • 基金资助:
    国家自然科学基金(No. 22471172)资助项目.

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*   

  1. 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:2026-04-22 Revised:2026-05-13
  • Contact: *E-mail: chaoliu@sit.edu.cn
  • Supported by:
    National Natural Science Foundation of China (No. 22471172).

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补充材料

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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

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