{"title":"Photooxidative C-C double bond cleavage of β-enaminocarbonyl compounds: toward selective <i>N</i>-formylation of amines.","authors":"Hayeon You, Suk Hyun Lim, Dae Won Cho","doi":"10.1039/d4ob01688b","DOIUrl":null,"url":null,"abstract":"<p><p>A photooxidative C-C double bond cleavage of electron-deficient β-enaminocarbonyl compounds possessing a silyl group at the α-position to the nitrogen atom using methylene blue (MB) as the photosensitizer was explored. Photochemically generated <sup>1</sup>O<sub>2</sub> was added across the CC bond with the aid of a tethered silyl group to cleave it and form <i>N</i>-formylamines. This reaction protocol exhibited compatibility with numerous β-enaminocarbonyl substrates, including those with various <i>N</i>-alkyl, <i>N</i>-benzyl and <i>N</i>-aryl substituents.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9000,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d4ob01688b","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
A photooxidative C-C double bond cleavage of electron-deficient β-enaminocarbonyl compounds possessing a silyl group at the α-position to the nitrogen atom using methylene blue (MB) as the photosensitizer was explored. Photochemically generated 1O2 was added across the CC bond with the aid of a tethered silyl group to cleave it and form N-formylamines. This reaction protocol exhibited compatibility with numerous β-enaminocarbonyl substrates, including those with various N-alkyl, N-benzyl and N-aryl substituents.