{"title":"用于合成二肽和酰胺的可见光诱导脱氧酰胺化协议","authors":"Ji-Wei Ren, Cheng-Shuai Han, Huai-Xin Zhang, Qing-Hao Zhang, Xian-Ting Song, Jing-Hui Sun","doi":"10.1039/d4qo00793j","DOIUrl":null,"url":null,"abstract":"A green and sustainable visible light-mediated deoxygenative amidation protocol to generate acyl radicals from commercially available carboxylic acids was described. The cheap, commercially available and user friendly organic photoredox catalyst, rhodamine B, could be employed in the dipeptide and amide coupling reactions under metal-free conditions by visible light irradiation. This method showed excellent functional selectivity for the formation of peptide bond or amide bond without affecting other functional groups such as alcohols, amides, halogens and heterocycles. This reaction was applicable to challenging amide coupling reactions of hindered carboxylic acids with low nucleophilic amines. The operationally straightforward method enriches the efficient synthesis of various dipeptides and amides in moderate to good yields (55-89%).","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":4.6000,"publicationDate":"2024-06-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Visible Light-Induced Deoxygenative Amidation Protocol for Synthesis of Dipeptide and Amide\",\"authors\":\"Ji-Wei Ren, Cheng-Shuai Han, Huai-Xin Zhang, Qing-Hao Zhang, Xian-Ting Song, Jing-Hui Sun\",\"doi\":\"10.1039/d4qo00793j\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"A green and sustainable visible light-mediated deoxygenative amidation protocol to generate acyl radicals from commercially available carboxylic acids was described. The cheap, commercially available and user friendly organic photoredox catalyst, rhodamine B, could be employed in the dipeptide and amide coupling reactions under metal-free conditions by visible light irradiation. This method showed excellent functional selectivity for the formation of peptide bond or amide bond without affecting other functional groups such as alcohols, amides, halogens and heterocycles. This reaction was applicable to challenging amide coupling reactions of hindered carboxylic acids with low nucleophilic amines. The operationally straightforward method enriches the efficient synthesis of various dipeptides and amides in moderate to good yields (55-89%).\",\"PeriodicalId\":97,\"journal\":{\"name\":\"Organic Chemistry Frontiers\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":4.6000,\"publicationDate\":\"2024-06-17\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic Chemistry Frontiers\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1039/d4qo00793j\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Chemistry Frontiers","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d4qo00793j","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Visible Light-Induced Deoxygenative Amidation Protocol for Synthesis of Dipeptide and Amide
A green and sustainable visible light-mediated deoxygenative amidation protocol to generate acyl radicals from commercially available carboxylic acids was described. The cheap, commercially available and user friendly organic photoredox catalyst, rhodamine B, could be employed in the dipeptide and amide coupling reactions under metal-free conditions by visible light irradiation. This method showed excellent functional selectivity for the formation of peptide bond or amide bond without affecting other functional groups such as alcohols, amides, halogens and heterocycles. This reaction was applicable to challenging amide coupling reactions of hindered carboxylic acids with low nucleophilic amines. The operationally straightforward method enriches the efficient synthesis of various dipeptides and amides in moderate to good yields (55-89%).
期刊介绍:
Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.