{"title":"β-烯氨基羰基化合物的光氧化 C-C 双键裂解：实现胺的选择性 N-甲酰化。","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":"{\"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}","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}
Photooxidative C-C double bond cleavage of β-enaminocarbonyl compounds: toward selective N-formylation of amines.
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.
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