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2021 , Vol. 41 >Issue 6: 2424 - 2434

DOI: https://doi.org/10.6023/cjoc202012022

研究论文

三氟甲磺酸铜(II)催化的硫醇对烯酮的共轭加成反应

  • 张同飞 ,
  • 陈逸波 ,
  • 高振博
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  • 南京农业大学理学院 南京 210095

收稿日期: 2020-12-14

  修回日期: 2020-12-06

  网络出版日期: 2021-02-26

基金资助

2020年国家级大学生创新训练计划(202010307090)

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Cu(OTf)2 Catalyzed Conjugate Addition of Mercaptans to Enones

  • Tongfei Zhang ,
  • Yibo Chen ,
  • Zhenbo Gao
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  • College of Sciences, Nanjing Agricultural University, Nanjing 210095
*Corresponding author.E-mail:

Received date: 2020-12-14

  Revised date: 2020-12-06

  Online published: 2021-02-26

Supported by

Nanjing Agricultural University Research Start-Up Funding, the Jiangsu Shuang Chuang Doctoral Grants in 2019, and the National Program for Student Innovation through Research and Training in 2020(202010307090)

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摘要

硫醚是一类具有重要生物和生理活性的化合物, 常见于药物以及天然产物中, 其高效合成方法是有机化学研究热点之一. 硫-共轭加成特别是有机小分子催化的加成反应的研究比较充分, 已被证明是一种合成硫醚分子的有效手段. 然而, 科研工作者对于过渡金属催化的硫-共轭加成反应的研究相对较少, 仍需要大量探索. 本工作通过借助三氟甲磺酸铜的催化, 实现了多类硫醇分子在环型、线型等多种迈克尔受体上的共轭加成反应, 高效合成了42种硫醚分子(产率最高可达99%). 该方法具有反应条件温和、底物广泛、操作简单以及产率优秀等众多优点, 为硫醚类分子的合成提供了新的方法.

关键词： 铜金属催化; 共轭加成; 硫醇

本文引用格式

张同飞 , 陈逸波 , 高振博 . 三氟甲磺酸铜(II)催化的硫醇对烯酮的共轭加成反应[J]. 有机化学, 2021 , 41(6) : 2424 -2434 . DOI: 10.6023/cjoc202012022

Abstract

Thioether is a class of compounds with important biological and physiological activities, especially for drugs and natural products, and its efficient synthesis method is one of the research hotspots in organic chemistry. Thia-Michael addition, especially the addition catalyzed by small organic molecules has been widely proved to be an effective method for synthesizing thioether molecules. However, very few studies on transition metal-catalyzed thia-Michael addition have been published and further exploration in this area is needed. In this work, different types of thiol molecules have been effectively added to various cyclic and linear Michael acceptors through the catalysis of copper(II) triflate. To our delight, 42 kinds of sulfide molecules (up to 99% yield) have been efficiently synthesized. This method has many advantages such as mild reaction conditions, wide substrates, simple operation and excellent yield, providing a new method for the preparation of various thioether molecules.

Key words： copper catalysis; conjugate addition; mercaptan

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