A visible light-induced deoxygenative amidation protocol for the synthesis of dipeptides and amides

被引:1
作者
Ren, Ji-Wei [1 ]
Han, Cheng-Shuai [1 ]
Zhang, Huai-Xin [1 ]
Zhang, Qing-Hao [1 ]
Song, Xian-Ting [1 ]
Sun, Jing-Hui [1 ]
机构
[1] Taishan Univ, Coll Chem & Chem Engn, Tai An 271000, Shandong, Peoples R China
来源
ORGANIC CHEMISTRY FRONTIERS | 2024年 / 11卷 / 16期
关键词
PEPTIDE COUPLING REAGENTS; CARBOXYLIC-ACIDS; DECARBOXYLATIVE REACTIONS; PHOTOREDOX CATALYSIS; PERSPECTIVE; ALDEHYDES; ACCESS;
D O I
10.1039/d4qo00793j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A green and sustainable visible light-mediated deoxygenative amidation protocol to generate acyl radicals from commercially available carboxylic acids is described. The cheap, commercially available and user friendly organic photoredox catalyst rhodamine B could be employed in dipeptide and amide coupling reactions under metal-free conditions and visible light irradiation. This method showed excellent functional group selectivity for the formation of peptide bonds or amide bonds without affecting other functional groups such as alcohols, amides, halogens and heterocycles. This protocol was suitable for use in challenging amide coupling reactions involving hindered carboxylic acids with low nucleophilic amines. This operationally straightforward method boosts the efficient synthesis of various dipeptides and amides in moderate to good yields (55-89%). A green and sustainable visible light-mediated deoxygenative amidation protocol to generate acyl radicals from carboxylic acids was developed to efficiently synthesize dipeptides and amides.
引用
收藏
页码:4449 / 4455
页数:7
相关论文
共 74 条
[1]   Choosing the Right Coupling Reagent for Peptides: A Twenty-Five-Year Journey [J].
Albericio, Fernando ;
El-Faham, Ayman .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2018, 22 (07) :760-772
[2]   Direct Use of Carboxylic Acids in the Photocatalytic Hydroacylation of Styrenes To Generate Dialkyl Ketones [J].
Alvarado, Jesus I. Martinez ;
Ertel, Alyssa B. ;
Stegner, Andrea ;
Stache, Erin E. ;
Doyle, Abigail G. .
ORGANIC LETTERS, 2019, 21 (24) :9940-9944
[3]   TCFH-NMI: Direct Access to N-Acyl Imidazoliums for Challenging Amide Bond Formations [J].
Beutner, Gregory L. ;
Young, Ian S. ;
Davies, Merrill L. ;
Hickey, Matthew R. ;
Park, Hyunsoo ;
Stevens, Jason M. ;
Ye, Qingmei .
ORGANIC LETTERS, 2018, 20 (14) :4218-4222
[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]   Mild, visible light-mediated decarboxylation of aryl carboxylic acids to access aryl radicals [J].
Candish, L. ;
Freitag, M. ;
Gensch, T. ;
Glorius, F. .
CHEMICAL SCIENCE, 2017, 8 (05) :3618-3622
[6]   Metallaphotoredox: The Merger of Photoredox and Transition Metal Catalysis [J].
Chan, Amy Y. ;
Perry, Ian B. ;
Bissonnette, Noah B. ;
Buksh, Benito F. ;
Edwards, Grant A. ;
Frye, Lucas, I ;
Garry, Olivia L. ;
Lavagnino, Marissa N. ;
Li, Beryl X. ;
Liang, Yufan ;
Mao, Edna ;
Millet, Agustin ;
Oakley, James, V ;
Reed, Nicholas L. ;
Sakai, Holt A. ;
Seath, Ciaran P. ;
MacMillan, David W. C. .
CHEMICAL REVIEWS, 2022, 122 (02) :1485-1542
[7]   Visible light-driven photocatalytic generation of sulfonamidyl radicals for alkene hydroamination of unsaturated sulfonamides [J].
Chen, Jun ;
Guo, Hong-Mei ;
Zhao, Quan-Qing ;
Chen, Jia-Rong ;
Xiao, Wen-Jing .
CHEMICAL COMMUNICATIONS, 2018, 54 (50) :6780-6783
[8]   Carboxylic Acids as A Traceless Activation Group for Conjugate Additions: A Three-Step Synthesis of (±)-Pregabalin [J].
Chu, Lingling ;
Ohta, Chisa ;
Zuo, Zhiwei ;
MacMillan, David W. C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (31) :10886-10889
[9]   Key green chemistry research areas - a perspective from pharmaceutical manufacturers [J].
Constable, David J. C. ;
Dunn, Peter J. ;
Hayler, John D. ;
Humphrey, Guy R. ;
Leazer, Johnnie L., Jr. ;
Linderman, Russell J. ;
Lorenz, Kurt ;
Manley, Julie ;
Pearlman, Bruce A. ;
Wells, Andrew ;
Zaks, Aleksey ;
Zhang, Tony Y. .
GREEN CHEMISTRY, 2007, 9 (05) :411-420
[10]   Peptide and amide bond-containing dendrimers [J].
Crespo, L ;
Sanclimens, G ;
Pons, M ;
Giralt, E ;
Royo, M ;
Albericio, F .
CHEMICAL REVIEWS, 2005, 105 (05) :1663-1681