Amidation of β-Keto Sulfonyl Fluorides via C-C Bond Cleavage

被引：2

作者：

Liang, Hui ^{[1
]}

Liu, Qian ^{[1
]}

Zhao, Xueyan ^{[1
]}

He, Tianyu ^{[1
]}

Luo, Jinyue ^{[1
]}

Huang, Shenlin ^{[1
,2
]}

机构：

[1] Nanjing Forestry Univ, Jiangsu Coinnovat Ctr Efficient Proc & Utilizat Fo, Nanjing 210037, Peoples R China

[2] Hunan Normal Univ, Coll Chem & Chem Engn, Key Lab Chem Biol & Tradit Chinese Med Res, Minist Educ China, Changsha 410081, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 27卷 / 27期

基金：

中国国家自然科学基金;

关键词：

amidation; amides; amines; C-N bond formation; sulfonyl fluorides; AMIDE;

D O I：

10.1002/ejoc.202400391

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple protocol for amide bond construction using beta-keto sulfonyl fluorides (BKSFs) as the acyl surrogates has been achieved. The reaction of BKSFs with a range of amines could be performed in presence of N-bromosuccinimide (NBS), affording various amides with diverse functionalities. Preliminary mechanistic studies revealed that the dibromo-substituted sulfonyl fluorides could be the key intermediate in this amidation process. A simple protocol has been developed for amide bond construction using beta-keto sulfonyl fluorides as the acyl surrogates. These readily available BKSFs can be reacted with a variety of amines in presence of N-bromosuccinimide, producing the desired amides with diverse functionalities. image

引用

页数：4

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