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

共 44 条

[1] Contemporary Approaches for Amide Bond Formation [J].

Acosta-Guzman, Paola ;

Ojeda-Porras, Andrea ;

Gamba-Sanchez, Diego .

ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (24) :4359-4391

[2] Electrochemical Amidation: Benzoyl Hydrazine/Carbazate and Amine as Coupling Partners [J].

Alam, Tipu ;

Rakshit, Amitava ;

Dhara, Hirendra Nath ;

Palai, Angshuman ;

Patel, Bhisma K. .

ORGANIC LETTERS, 2022, 24 (36) :6619-6624

[3]

[Anonymous], 2011, J CHEM RES, V35, P298

[4] Analysis of Past and Present Synthetic Methodologies on Medicinal Chemistry: Where Have All the New Reactions Gone? [J].

Brow, Dean G. ;

Bostrom, Jonas .

JOURNAL OF MEDICINAL CHEMISTRY, 2016, 59 (10) :4443-4458

[5] Cooperativity of steric bulk and H-bonding in coordination sphere engineering: heteroleptic PdII cages and bowls by design [J].

Chen, Bin ;

Holstein, Julian J. ;

Platzek, Andre ;

Schneider, Laura ;

Wu, Kai ;

Clever, Guido H. .

CHEMICAL SCIENCE, 2022, 13 (06) :1829-1834

[6] Electrochemical Oxo-Fluorosulfonylation of Alkynes under Air: Facile Access to β-Keto Sulfonyl Fluorides [J].

Chen, Dengfeng ;

Nie, Xingliang ;

Feng, Qingyuan ;

Zhang, Yingyin ;

Wang, Yiheng ;

Wang, Qiuyue ;

Huang, Lin ;

Huang, Shenlin ;

Liao, Saihu .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (52) :27271-27276

[7] Water as the reaction medium in organic chemistry: from our worst enemy to our best friend [J].

Cortes-Clerget, Margery ;

Yu, Julie ;

Kincaid, Joseph R. A. ;

Walde, Peter ;

Gallou, Fabrice ;

Lipshutz, Bruce H. .

CHEMICAL SCIENCE, 2021, 12 (12) :4237-4266

[8] Nonclassical Routes for Amide Bond Formation [J].

de Figueiredo, Renata Marcia ;

Suppo, Jean-Simon ;

Campagne, Jean-Marc .

CHEMICAL REVIEWS, 2016, 116 (19) :12029-12122

[9] Sulfur(VI) Fluoride Exchange (SuFEx): Another Good Reaction for Click Chemistry [J].

Dong, Jiajia ;

Krasnova, Larissa ;

Finn, M. G. ;

Sharpless, K. Barry .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (36) :9430-9448

[10] C-C Fragmentation: Origins and Recent Applications [J].

Drahl, Michael A. ;

Manpadi, Madhuri ;

Williams, Lawrence J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (43) :11222-11251

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