Hai-Bing Ye , Ye-Peng Bao , Tian-Yang Liu , Tao Wei , Chen Yang , Qing-An Liu , Jun Xuan
{"title":"Photoredox-enabled remote radical group migration: Pathway to 1,7-dicarbonyl compounds from diazoalkanes","authors":"Hai-Bing Ye , Ye-Peng Bao , Tian-Yang Liu , Tao Wei , Chen Yang , Qing-An Liu , Jun Xuan","doi":"10.1016/j.tchem.2023.100040","DOIUrl":null,"url":null,"abstract":"<div><p>Herein, we developed a mild and efficient photoredox-enabled remote radical group migration with the utilization of diazoalkanes as radical precursors, giving access to various valuable 1,7-dicarbonlys in moderate to good yields. A diverse set of migrating groups, including benzothiazole, benzothiophene, pyrazine, pyridine, thiazole, thiophene and nitrile were well tolerated. Furthermore, the facile synthesis of 1,8-dicarbonyl compound, scale-up reaction and useful synthetic transformation further proved the method attractive and valuable.</p></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"7 ","pages":"Article 100040"},"PeriodicalIF":0.0000,"publicationDate":"2023-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron chem","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S2666951X23000062","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0
Abstract
Herein, we developed a mild and efficient photoredox-enabled remote radical group migration with the utilization of diazoalkanes as radical precursors, giving access to various valuable 1,7-dicarbonlys in moderate to good yields. A diverse set of migrating groups, including benzothiazole, benzothiophene, pyrazine, pyridine, thiazole, thiophene and nitrile were well tolerated. Furthermore, the facile synthesis of 1,8-dicarbonyl compound, scale-up reaction and useful synthetic transformation further proved the method attractive and valuable.