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2020 , Vol. 40 >Issue 7: 1926 - 1933

DOI: https://doi.org/10.6023/cjoc202003004

研究论文

Selectfluor作用下二芳基二硫醚和醇的双亚磺酰化反应制备亚磺酸酯

  • 刘爱遥 ,
  • 刘江 ,
  • 梅海波 ,
  • Gerd-Volker Röschenthaler ,
  • 韩建林
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  • a 南京林业大学化学工程学院 江苏省林业资源高效加工利用协调创新中心 南京 210037;
    b 青岛科技大学化学与分子工程学院 山东省生化分析重点实验室 青岛 266042;
    c 不来梅雅各布大学生命科学与化学学院 不来梅 28759

收稿日期: 2020-03-03

  修回日期: 2020-05-06

  网络出版日期: 2020-05-15

基金资助

国家自然科学基金（No.21761132021）、德国研究基金（No.362/74-1）和青岛科技大学化学学部开放课题（No.QUSTHX202005）资助项目.

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Selectfluor-Promoted Twofold Sulfination of Alcohols for the Synthesis of Sulfinic Ester from Diaryldisulfides

  • Liu Aiyao ,
  • Liu Jiang ,
  • Mei Haibo ,
  • Röschenthaler Gerd-Volker ,
  • Han Jianlin
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  • a Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China;
    b Shandong Key Laboratory of Biochemical Analysis, College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, China;
    c Department of Life Sciences and Chemistry, Jacobs University Bremen gGmbH, Bremen 28759, Germany

Received date: 2020-03-03

  Revised date: 2020-05-06

  Online published: 2020-05-15

Supported by

Project supported by the National Natural Science Foundation of China (No. 21761132021), the German Research Foundation (No. 362/74-1) and the Open Project of Chemistry Department of Qingdao University of Science and Technology (No. QUSTHX202005).

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摘要

报道了一种新型的由二芳基二硫醚和醇双亚磺酰化反应来制备亚磺酸酯的方法.在Selectfluor作为氧化剂的条件下，一分子二硫醚与两分子醇反应，能够顺利转化得到两分子亚磺酸酯产物.该反应无需金属催化剂，在简单温和的条件下即可进行，反应产率很高.反应底物适用性广，含有不同取代基的二硫醚和醇，包括天然的手性醇类化合物，均能很好地发生反应得到相应的产物.该方法实现了简单条件下通过醇的亚磺酰化反应高效地构建亚磺酸酯，为亚磺酸酯及其衍生物的合成提供了一条新的途径.

关键词： Selectfluor; 二硫醚; 亚磺酰化; 亚磺酸酯; C—O键断裂

本文引用格式

刘爱遥 , 刘江 , 梅海波 , Gerd-Volker Röschenthaler , 韩建林 . Selectfluor作用下二芳基二硫醚和醇的双亚磺酰化反应制备亚磺酸酯[J]. 有机化学, 2020 , 40(7) : 1926 -1933 . DOI: 10.6023/cjoc202003004

Abstract

An oxidative twofold sulfination of alcohol with Selectfluor as an efficient oxidant was developed. This reaction proceeded smoothly achieving the unprecedented sulfination transformation of varieties of diaryldisulfides and alcohols under simple conditions, affording the corresponding sulfinic esters in excellent yields. The current reaction provides a new and convenient strategy for the preparation of sulfinic esters.

Key words： Selectfluor; disulfide; sufination; sulfinic ester; C-O bond cleavage

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