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2024 , Vol. 44 >Issue 7: 2363 - 2370

DOI: https://doi.org/10.6023/cjoc202312022

研究论文

邻二碘芳烃和氢化钠产生芳炔用于硫醇的邻碘芳基化反应

  • 刘典范 ,
  • 王健智 ,
  • 王梦晴 ,
  • 陈晓蓓 ,
  • 胡延维 ,
  • 张士磊
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  • 苏州大学药学院 江苏省重大神经精神疾病研究重点实验室 江苏省精准诊疗药物创制工程研究中苏苏州 215123

收稿日期: 2023-12-23

  修回日期: 2024-03-08

  网络出版日期: 2024-03-20

基金资助

国家自然科学基金(22271206); 国家自然科学基金(22071053); 江苏省高校重点学科建设(PAPD); 苏州市脑病诊疗国际联合实验室资助项目

收起

o-Iodoarylation of Thiols Enabled by Aryne Generated from o-Diiodoarene and Sodium Hydride

  • Dianfan Liu ,
  • Jianzhi Wang ,
  • Mengqing Wang ,
  • Xiaobei Chen ,
  • Yanwei Hu ,
  • Shilei Zhang
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  • Jiangsu Key Laboratory of Neuropsychiatric Diseases, Jiangsu Province Engineering Research Center of Precision Diagnostics and Therapeutics Development, College of Pharmaceutical Sciences,Soochow University, Suzhou, Jiangsu 215123
* E-mail: ;

Received date: 2023-12-23

  Revised date: 2024-03-08

  Online published: 2024-03-20

Supported by

National Natural Science Foundation of China(22271206); National Natural Science Foundation of China(22071053); Priority Academic Program Development of Jiangsu Higher Education Institutions(PAPD); Suzhou International Joint Laboratory for Diagnosis and Treatment of Brain Diseases.

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摘要

该方法使用廉价易得的试剂邻二碘芳烃和氢化钠生成苯炔, 然后与硫醇发生反应, 简单高效地合成邻碘芳基硫醚. 值得注意的是, 在反应中没有观察到像过渡金属催化那样得到的二硫醚副产物. 该方法操作简单, 条件温和, 底物范围广泛, 很多情况下都给出较高收率的产物.

关键词： 芳炔; 硫醇; 邻二碘芳烃; 氢化钠; 邻碘芳基硫醚

本文引用格式

刘典范 , 王健智 , 王梦晴 , 陈晓蓓 , 胡延维 , 张士磊 . 邻二碘芳烃和氢化钠产生芳炔用于硫醇的邻碘芳基化反应[J]. 有机化学, 2024 , 44(7) : 2363 -2370 . DOI: 10.6023/cjoc202312022

Abstract

A simple and efficient method is described for the synthesis of o-iodoaryl thioethers by the reaction of thiols and aryne. The aryne is generated from inexpensive and readily available reagents o-diiodoarene and sodium hydride. Remarkably, no disulfide substituted byproduct was observed in the reactions which is different from transition metal-catalyzed process. This method features simple operation, mild reaction conditions, broad substrate scope, and high reaction yields for many cases.

Key words： aryne; thiol; o-diiodoarene; sodium hydride; o-iodoaryl thioether

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