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2024 , Vol. 44 >Issue 2: 533 - 549

DOI: https://doi.org/10.6023/cjoc202310005

研究论文

亚硝酸异戊酯活化伯磺酰胺制备磺酰溴与磺酰氯

  • 江港钟 ,
  • 林嘉欣 ,
  • 鲍晓光 ,
  • 万小兵
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  • 苏州大学材料与化学化工学部 江苏苏州 215123

收稿日期: 2023-10-07

  修回日期: 2023-11-02

  网络出版日期: 2023-11-08

基金资助

国家自然科学基金(21973068); 国家自然科学基金(21971175)

收起

Isoamyl Nitrite Activated Primary Sulfonamide to Sulfonyl Bromide and Sulfonyl Chloride

  • Gangzhong Jiang ,
  • Jiaxing Lin ,
  • Xiaoguang Bao ,
  • Xiaobing Wan
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  • College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, Jiangsu 215123
* Corresponding authorss. E-mail: ;

Received date: 2023-10-07

  Revised date: 2023-11-02

  Online published: 2023-11-08

Supported by

Natural Science Foundation of China(21973068); Natural Science Foundation of China(21971175)

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摘要

磺酰溴与磺酰氯是一类十分重要的化合物, 是有机转换中常用的合成砌块. 以亚硝酸异戊酯(iAmONO)为活化剂, 二溴海因(DBDMH)为溴源或三氯异氰尿酸(TCCA)为氯源, 实现了伯磺酰胺(包含药物分子)到磺酰溴或磺酰氯的合成转换. 该方法具有原料来源广泛、底物普适性好、收率优良以及条件温和等优点, 不仅能进行克级制备, 还能进行一系列后期官能团衍生, 具有良好的实用价值. 机理研究表明, N,N-二卤磺酰胺是该方法可能的中间体, 亚硝酸异戊酯在该转化过程中起到了至关重要的作用.

关键词： 伯磺酰胺; 亚硝酸异戊酯; 磺酰溴; 磺酰氯

本文引用格式

江港钟 , 林嘉欣 , 鲍晓光 , 万小兵 . 亚硝酸异戊酯活化伯磺酰胺制备磺酰溴与磺酰氯[J]. 有机化学, 2024 , 44(2) : 533 -549 . DOI: 10.6023/cjoc202310005

Abstract

Sulfonyl bromide and sulfonyl chloride are important compounds commonly used as building blocks in organic synthesis. This paper presents the successful synthesis of sulfonyl bromide or sulfonyl chloride from primary sulfonamide using isoamyl nitrite (iAmONO) as an activator, dibromantine (DBDMH) as a bromine source, or trichloroisocyanuric acid (TCCA) as a chlorine source. The method offers several advantages such as wide range of raw materials, compatibility with various substrates, high yield, and mild reaction conditions. It is suitable for both gram-scale preparations and subsequent derivations, demonstrating practical value. Mechanistic studies suggest that N,N-dihalosulfonamide is a potential intermediate in this process and isoamyl nitrite plays a crucial role in the conversion process.

Key words： primary sulfonamide; isoamyl nitrite; sulfonyl bromide; sulfonyl chloride

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