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DOI: https://doi.org/10.6023/cjoc202605022

研究论文

无过渡金属条件下α-溴代腈与硫代磺酸酯的反应研究：合成α-砜基-α-芳/烷硫基腈

  • 张宇杭 ,
  • 杨益民 ,
  • 姜佳佳 ,
  • 姚秋丽 ,
  • 黄洋
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  • 遵义医科大学药学院 贵州省化学药物创制全省重点实验室 贵州遵义 563003

收稿日期: 2026-05-20

  修回日期: 2026-07-20

  网络出版日期: 2026-08-28

基金资助

遵义医科大学(No. F-1119)、贵州省教育厅自然科学研究项目([2024]334)资助

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Transition-Metal-Free Reaction of α-Bromonitriles with Thiosulfonates: Synthesis of α-Sulfonyl-α-(aryl/alkylthio)nitriles

  • Zhang Yuhang ,
  • Yang Yimin ,
  • Jiang Jiajia ,
  • Yao Qiuli ,
  • Huang Yang
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  • Guizhou Provincial Key Laboratory of Innovation and Manufacturing for Pharmaceuticals, School of Pharmacy, Zunyi Medical University, Zunyi, Guizhou 563003

Received date: 2026-05-20

  Revised date: 2026-07-20

  Online published: 2026-08-28

Supported by

Zunyi Medical University (No. F-1119), Natural Science Research Project of Guizhou Provincial Department of Education (No. [2024]334).

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摘要

本研究报道了一种在无需过渡金属催化的条件下,硫代磺酸酯与α‐溴代腈的双官能团取代反应高效合成α-砜基-α-芳/烷硫基腈。该方法通过一步反应即可在氰基α-位同时构建两种不同的碳‐硫键,从而为构建含有氰基、磺酰基及芳/烷硫基官能团的全碳季碳中心提供了一种新策略。该方法表现出良好的底物普适性和官能团兼容性,无论是含有吸电子基团还是给电子基团的取代底物,均能以中等至优异的产率得到相应的α-砜基-α-芳/烷硫基腈,具有反应条件温和、操作简便、原子经济性高等优点。

关键词： α-溴代腈; 硫代磺酸酯; 双官能团化; α-砜基-α-芳/烷硫基腈

本文引用格式

张宇杭 , 杨益民 , 姜佳佳 , 姚秋丽 , 黄洋 . 无过渡金属条件下α-溴代腈与硫代磺酸酯的反应研究：合成α-砜基-α-芳/烷硫基腈[J]. 有机化学, 0 : 0 . DOI: 10.6023/cjoc202605022

Abstract

We report a transition-metal-free difunctionalization reaction of thiosulfonates with α-bromonitriles, enabling the efficient synthesis of α-sulfonyl-(aryl/alkylthio)nitrile derivatives. In a single step, this protocol simultaneously constructs two distinct carbon-sulfur bonds at the α-position of the cyano group, thereby providing a new approach to all-carbon quaternary centers bearing cyano, sulfonyl, and aryl/alkylthio groups. The method exhibits broad substrate scope and excellent functional-group tolerance: substrates bearing either electron-withdrawing or electron-donating substituents afford the corresponding α-sulfonyl-α-(aryl/alkylthio)nitrile derivatives in moderate to excellent yields. Notably, this protocol features mild reaction conditions, operational simplicity, and high atom economy.

Key words： α-bromonitriles; thiosulfonates; difunctionalization; α-sulfonyl-α-(aryl/alkylthio)nitrile

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