用 CX3SO2Cl 进行催化剂和无碱可见光驱动的自由基中继三卤甲基化/官能团迁移/羰基化反应

IF 2.7 3区化学 Q1 CHEMISTRY, ORGANIC

Organic & Biomolecular Chemistry Pub Date : 2024-06-05 DOI:10.1039/d4ob00292j

Jinkai Hu , Chenglei Yang , Xiaotao Qin , Hui Liu , Tongtong Ma , Ao-tong Shi , Qing-Long Lv , Xingman Liu , Jinhui Yang , Dianjun Li

{"title":"用 CX3SO2Cl 进行催化剂和无碱可见光驱动的自由基中继三卤甲基化/官能团迁移/羰基化反应","authors":"Jinkai Hu , Chenglei Yang , Xiaotao Qin , Hui Liu , Tongtong Ma , Ao-tong Shi , Qing-Long Lv , Xingman Liu , Jinhui Yang , Dianjun Li","doi":"10.1039/d4ob00292j","DOIUrl":null,"url":null,"abstract":"<div>Herein, we report a visible light-enabled radical trihalomethylation/cyano-migration/carbonylation cascade reaction of 2-hydroxy-2-hex-5-enenitrile with CX3SO2Cl as the CX3-source (X = F, Cl) to obtain 5-oxo-2-(2,2,2-trihaloethyl)pentanenitrile compounds in the absence of a photocatalyst, transition metal and base. This reaction system is also effective to convert (benzo[d]thiazol-2-yl)-pent-4-enol to the corresponding 4-(benzo[d]thiazol-2-yl)-6,6,6-trihalo-hexanone products. These reactions occur under mild conditions, tolerate a wide range of functional groups, and provide alternative approaches for the 1,2-bifunctionalization reaction of unactivated olefins.</div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":"22 22","pages":"Pages 4488-4493"},"PeriodicalIF":2.7000,"publicationDate":"2024-06-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Catalyst- and base-free visible light-enabled radical relay trihalomethylation/functional group-migration/carbonylation with CX3SO2Cl†\",\"authors\":\"Jinkai Hu , Chenglei Yang , Xiaotao Qin , Hui Liu , Tongtong Ma , Ao-tong Shi , Qing-Long Lv , Xingman Liu , Jinhui Yang , Dianjun Li\",\"doi\":\"10.1039/d4ob00292j\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div>Herein, we report a visible light-enabled radical trihalomethylation/cyano-migration/carbonylation cascade reaction of 2-hydroxy-2-hex-5-enenitrile with CX3SO2Cl as the CX3-source (X = F, Cl) to obtain 5-oxo-2-(2,2,2-trihaloethyl)pentanenitrile compounds in the absence of a photocatalyst, transition metal and base. This reaction system is also effective to convert (benzo[d]thiazol-2-yl)-pent-4-enol to the corresponding 4-(benzo[d]thiazol-2-yl)-6,6,6-trihalo-hexanone products. These reactions occur under mild conditions, tolerate a wide range of functional groups, and provide alternative approaches for the 1,2-bifunctionalization reaction of unactivated olefins.</div>\",\"PeriodicalId\":96,\"journal\":{\"name\":\"Organic & Biomolecular Chemistry\",\"volume\":\"22 22\",\"pages\":\"Pages 4488-4493\"},\"PeriodicalIF\":2.7000,\"publicationDate\":\"2024-06-05\",\"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/S1477052024004464\",\"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://www.sciencedirect.com/org/science/article/pii/S1477052024004464","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

摘要

在此，我们报告了在没有光催化剂、过渡金属和碱的情况下，以 CX3SO2Cl 为 CX3 源（X = F、Cl），利用可见光使 2-羟基-2-己-5-烯腈发生自由基三卤甲基化/氰基迁移/羰基化级联反应，从而得到 5-氧代-2-(2,2,2-三卤乙基)戊腈化合物。该反应体系还能有效地将（苯并[d]噻唑-2-基）-戊-4-烯醇转化为相应的 4-（苯并[d]噻唑-2-基）-6,6,6-三卤代己酮产品。这些反应在温和的条件下进行，可容忍多种官能团，为未活化烯烃的 1,2-双官能化反应提供了替代方法。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Catalyst- and base-free visible light-enabled radical relay trihalomethylation/functional group-migration/carbonylation with CX3SO2Cl†

查看原文本刊更多论文

Catalyst- and base-free visible light-enabled radical relay trihalomethylation/functional group-migration/carbonylation with CX3SO2Cl†

Herein, we report a visible light-enabled radical trihalomethylation/cyano-migration/carbonylation cascade reaction of 2-hydroxy-2-hex-5-enenitrile with CX₃SO₂Cl as the CX₃-source (X = F, Cl) to obtain 5-oxo-2-(2,2,2-trihaloethyl)pentanenitrile compounds in the absence of a photocatalyst, transition metal and base. This reaction system is also effective to convert (benzo[d]thiazol-2-yl)-pent-4-enol to the corresponding 4-(benzo[d]thiazol-2-yl)-6,6,6-trihalo-hexanone products. These reactions occur under mild conditions, tolerate a wide range of functional groups, and provide alternative approaches for the 1,2-bifunctionalization reaction of unactivated olefins.

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.