高等学校化学学报

高等学校化学学报

• 研究论文 • 上一篇    下一篇

芳基噻嗯盐分子内选择性C-S键断裂合成苯并硫醚

南江,许凯伦,闫强   

  1. 陕西科技大学
  • 收稿日期:2024-12-11 修回日期:2025-02-06 出版日期:2025-02-14 发布日期:2025-02-14
  • 通讯作者: 南江 E-mail:nanjiang@sust.edu.cn
  • 基金资助:
    国家自然科学基金(批准号：22171171)、陕西省青年科技新星(批准号：2022KJXX-15)与陕西省科协人才托举(批准号：20200605)项目资助

Synthesis of Benzo-Thioethers Based on Intramolecular Selective C-S Cleavage of Arylthianthreniums

NAN Jiang，XU Kailun，YAN Qiang   

  1. Shaanxi University of Science and Technology
  • Received:2024-12-11 Revised:2025-02-06 Online:2025-02-14 Published:2025-02-14
  • Contact: Jiang Nan E-mail:nanjiang@sust.edu.cn
  • Supported by:
    Supported by the National Natural Science Foundation(No.22171171)，Innovative Talent Promotion Plan-Young Science and Technology Star Project (No.2022KJXX-15), and Shaanxi Provincial Association for Science and Technology (No.20200605)

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摘要： 本文提出了一种分子内芳基噻蒽盐亲核取代环化反应，通过C-O键与C-S的选择性断裂，实现了芳基噻嗯盐的新化学转化，高效合成了一系列高共轭的三苯并中环硫醚化合物. 该反应官能团兼容性优秀、产物收率高且无需过渡金属参与，合成了23例结构新颖的九元硫醚分子，为在催化反应中应用广泛的冠醚合成提供了一种新途径.

关键词: 芳基噻蒽盐, C—S键断裂, 苯并硫醚

Abstract: Here reported is an intramolecular nucleophilic substitution reaction of aryl-thianthrenium salts, which conducts the selective cleavage of C-O and C-S chemical bonds. This finding represents a novel chemical property and conversion with aryl-thianthreniums, rapidly assembling the highly conjugated tribenzo-thioester compounds. Of note, this developed methodology is charactered by excellent functional group tolerance, good productivities, and metal-free trait. This conversion delivers 23 examples of structurally innovative nine-membered thioethers, which puts forward an alternative synthesizing route for the widely used crown ethers.

Key words: Arylthianthreniums; C—S Bond cleavage, Benzo-thioesters

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