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
[21]   Synthesis of dibenzocycloketones by acyl radical cyclization from aromatic carboxylic acids using methylene blue as a photocatalyst [J].
Jiang, Hongshuo ;
Mao, Guijie ;
Wu, Hongfeng ;
An, Qi ;
Zuo, Minghui ;
Guo, Weihao ;
Xu, Chunzhao ;
Sun, Zhizhong ;
Chu, Wenyi .
GREEN CHEMISTRY, 2019, 21 (19) :5368-5373
[22]   Cooperative photoredox catalysis [J].
Lang, Xianjun ;
Zhao, Jincai ;
Chen, Xiaodong .
CHEMICAL SOCIETY REVIEWS, 2016, 45 (11) :3026-3038
[23]   Visible-Light-Induced Deoxygenative Acylation Aromatization of p-Quinone Methides with Carboxylic Acids [J].
Li, Guan-Nan ;
Li, Hao-Cong ;
Wang, Meng-Ru ;
Lu, Zhan ;
Yu, Bing .
ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (22) :3927-3931
[24]   Radical difluoromethylthiolation of aromatics enabled by visible light [J].
Li, Jianbin ;
Zhu, Dianhu ;
Lv, Leiyang ;
Li, Chao-Jun .
CHEMICAL SCIENCE, 2018, 9 (26) :5781-5786
[25]   Visible light-enabled selective depolymerization of oxidized lignin by an organic photocatalyst [J].
Li, Shuyuan ;
Hao, Zhongkai ;
Wang, Kaixuan ;
Tong, Min ;
Yang, Yanan ;
Jiang, Huating ;
Xiao, Yao ;
Zhang, Fang .
CHEMICAL COMMUNICATIONS, 2020, 56 (76) :11243-11246
[26]   Catalytic amide formation from non-activated carboxylic acids and amines [J].
Lundberg, Helena ;
Tinnis, Fredrik ;
Selander, Nicklas ;
Adolfsson, Hans .
CHEMICAL SOCIETY REVIEWS, 2014, 43 (08) :2714-2742
[27]   Polyamides - Still Strong After Seventy Years [J].
Marchildon, Keith .
MACROMOLECULAR REACTION ENGINEERING, 2011, 5 (01) :22-54
[28]   Visible-Light Photocatalysis: Does It Make a Difference in Organic Synthesis? [J].
Marzo, Leyre ;
Pagire, Santosh K. ;
Reiser, Oliver ;
Koenig, Burkhard .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (32) :10034-10072
[29]   Amide Bond Formation Strategies: Latest Advances on a Dateless Transformation [J].
Massolo, Elisabetta ;
Pirola, Margherita ;
Benaglia, Maurizio .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (30) :4641-4651
[30]   Synthesis of γ-Oxo-α-amino Acids via Radical Acylation with Carboxylic Acids [J].
Merkens, Kay ;
Troyano, Francisco Jose Aguilar ;
Anwar, Khadijah ;
Gomez-Suarez, Adrian .
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (12) :8448-8456