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
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页数：4
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