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2022 , Vol. 42 >Issue 1: 200 - 207

DOI: https://doi.org/10.6023/cjoc202106012

研究论文

碘催化乙烯基叠氮与芳基亚磺酸钠反应合成β-磺酰基烯胺

  • 刘锐凯 ,
  • 许峥 ,
  • 宁志涛 ,
  • 杜正银
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  • 西北师范大学化学化工学院 兰州 730070

收稿日期: 2021-06-06

  修回日期: 2021-08-11

  网络出版日期: 2021-09-08

基金资助

国家自然科学基金(21262028); 国家自然科学基金(21762039); 甘肃省自然科学基金(20JR5RA521)

收起

Synthesis of β-Sulfonyl Enamines via Iodine-Catalyzed Reaction between Vinyl Azides and Sodium Arylsulfinates

  • Ruikai Liu ,
  • Zheng Xu ,
  • Zhitao Ning ,
  • Zhengyin Du
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  • College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070
* Corresponding author. E-mail:

Received date: 2021-06-06

  Revised date: 2021-08-11

  Online published: 2021-09-08

Supported by

National Natural Science Foundation of China(21262028); National Natural Science Foundation of China(21762039); Natural Science Foundation of Gansu Province(20JR5RA521)

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摘要

发展了一种使用廉价碘单质作为催化剂, 乙烯基叠氮作为自由基受体, 芳基亚磺酸钠作为自由基源, 合成Z型结构的N-未保护的β-磺酰基烯胺类化合物的方法. 该反应中乙醇作为溶剂, 双三氟甲烷磺酰亚胺(Tf2NH)作为添加剂, 在40 ℃下反应4~6 h, 可以以优良的产率得到β-磺酰基烯胺类化合物. 该方法无需使用金属催化剂, 具有条件简单、反应时间短、底物适用范围广等优点.

关键词： 碘催化; 乙烯基叠氮; 自由基加成; 磺酰基烯胺

本文引用格式

刘锐凯 , 许峥 , 宁志涛 , 杜正银 . 碘催化乙烯基叠氮与芳基亚磺酸钠反应合成β-磺酰基烯胺[J]. 有机化学, 2022 , 42(1) : 200 -207 . DOI: 10.6023/cjoc202106012

Abstract

The present protocol provides the facile and highly efficient synthesis of various Z-structure N-unprotected β-sulfonyl enamine compounds in a manner by using inexpensive molecular iodine as catalyst, vinyl azides as free radical acceptor, and sodium arylsulfinates as free radical sources. In this reaction, ethanol was used as solvent and bistrifluoromethanesulfonimide (Tf2NH) was used as additive. The reaction was carried out at 40 ℃ for 4~6 h to obtain β-sulfonyl enamine compounds with good yields. The method does not need to use metal catalyst, and has the advantages of simple conditions, short reaction time and wide substrate application range.

Key words： iodine catalysis; vinyl azide; free radical addition; sulfonyl enamine

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