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。

IF 2.8 3区化学 Q1 CHEMISTRY, ORGANIC Organic & Biomolecular Chemistry Pub Date : 2024-11-07 Epub Date: 2024-11-11 DOI:10.1039/d4ob01688b

Hayeon You , Suk Hyun Lim , Dae Won Cho

{"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":"<div><div>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 <em>N</em>-formylamines. This reaction protocol exhibited compatibility with numerous β-enaminocarbonyl substrates, including those with various <em>N</em>-alkyl, <em>N</em>-benzyl and <em>N</em>-aryl substituents.</div></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":"23 1","pages":"Pages 108-112"},"PeriodicalIF":2.8000,"publicationDate":"2024-11-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Photooxidative C–C double bond cleavage of β-enaminocarbonyl compounds: toward selective N-formylation of amines†\",\"authors\":\"Hayeon You , Suk Hyun Lim , Dae Won Cho\",\"doi\":\"10.1039/d4ob01688b\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>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 <em>N</em>-formylamines. This reaction protocol exhibited compatibility with numerous β-enaminocarbonyl substrates, including those with various <em>N</em>-alkyl, <em>N</em>-benzyl and <em>N</em>-aryl substituents.</div></div>\",\"PeriodicalId\":96,\"journal\":{\"name\":\"Organic & Biomolecular Chemistry\",\"volume\":\"23 1\",\"pages\":\"Pages 108-112\"},\"PeriodicalIF\":2.8000,\"publicationDate\":\"2024-11-07\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic & Biomolecular Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S1477052024009911\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2024/11/11 0:00:00\",\"PubModel\":\"Epub\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1477052024009911","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/11/11 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}

引用次数: 0

摘要

以亚甲基蓝（MB）为光敏剂，对在氮原子的 α 位上具有硅基的缺电子 β-enaminocarbonyl 化合物的 C-C 双键的光氧化裂解进行了探索。光化学生成的 1O2 被添加到 CC 键上，借助系链硅基将其裂解并形成 N-甲酰胺。该反应方案与多种 β-烯氨基羰基底物兼容，包括具有各种 N-烷基、N-苄基和 N-芳基取代基的底物。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

摘要图片

查看原文

微信好友朋友圈 QQ好友复制链接

本刊更多论文

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.

求助全文

通过发布文献求助，成功后即可免费获取论文全文。去求助

来源期刊

Organic & Biomolecular Chemistry 化学-有机化学

CiteScore

5.50

自引率

9.40%

发文量

1056

审稿时长

1.3 months

期刊介绍： Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.