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2020 , Vol. 40 >Issue 8: 2483 - 2490

DOI: https://doi.org/10.6023/cjoc201912045

研究论文

原位产生二氧化锰催化构建S—S键

  • 吕进强 ,
  • 曾竟 ,
  • 阿布都热西提·阿布力克木
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  • 新疆师范大学化学系 乌鲁木齐 830054

收稿日期: 2019-12-31

  修回日期: 2020-05-12

  网络出版日期: 2020-05-19

基金资助

新疆维吾尔自治区高校科研计划自然科学重点项目（No.XJEDU2020I015）和新疆维吾尔自治区2017年自治区“天山青年计划”（No.2017Q026）资助项目.

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Highly Active Manganese Dioxide Catalyzed the Construction of S-S Bond

  • Lü Jinqiang ,
  • Zeng Jing ,
  • Abulikemu Abudu Rexit
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  • Department of Chemistry, Xinjiang Normal University, Urumqi 830054

Received date: 2019-12-31

  Revised date: 2020-05-12

  Online published: 2020-05-19

Supported by

Project supported by the Scientific Research Program of the Higher Education Institution of Xinjiang (No. XJEDU2020I015), and the Xinjiang Tianshan Youth Program (No. 2017Q026).

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摘要

利用0.1~0.2 equiv.高锰酸钾在无水乙醇体系中原位生成高活性二氧化锰，并以此为催化剂，促使硫酚、硫醇类化合物在室温下发生自由基自身偶联反应构建S—S键，获得了14种对称双硫化物，产率介于70%~99%；同时发现该催化体系还可催化对称双硫化物与不同取代基的硫酚、硫醇或两个不同的对称双硫化物，发生自由基交叉偶联反应合成了13个不对称双硫化合物，产率19%~72%.该法具有简单高效、后处理简单、绿色溶剂、底物适用范围广、条件温和等优点，所有产物均经1H NMR、13C NMR结构确证.

关键词： 自由基偶联反应; S-S键; 二氧化锰

本文引用格式

吕进强 , 曾竟 , 阿布都热西提·阿布力克木 . 原位产生二氧化锰催化构建S—S键[J]. 有机化学, 2020 , 40(8) : 2483 -2490 . DOI: 10.6023/cjoc201912045

Abstract

Generation of highly active manganese dioxide in situ by using catalytic amount of potassium permanganate in anhydrous ethanol system, the catalytic system promoted S-S bond construction by free radical self coupling reactions of thiophenol and mercaptan compounds at room temperature. 14 disulfides were obtained with 70%~99% yields. At the same time, it was also found that the catalytic system could also catalyze radical cross-coupling reactions between symmetric disulfides and different substituents of thiophenols, thiols, or two different symmetric disulfides, 13 asymmetric disulfides were obtained with 19%~72% yields. The protocol offered the advantages of simple and efficient, easy separation, green solvent, wide range of substrate applications, and mild conditions. All products were confirmed by 1H NMR and 13C NMR spectra.

Key words： free radical coupling reaction; S-S bond; manganese dioxide

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