{"title":"Iodobenzene-catalyzed photochemical heteroarylation of alcohols by rupture of inert C–H and C–C bonds","authors":"Zhu Cao , Xinxin Wang , Xinxin Wu , Chen Zhu","doi":"10.1016/j.tchem.2022.100031","DOIUrl":null,"url":null,"abstract":"<div><p>A Minisci-type reaction catalyzed by iodobenzene is disclosed here for the first time. The heteroarylation of unprotected aliphatic alcohols proceeds via alkoxy radical-induced homolytic cleavage of C–H and C–C bonds under photochemical conditions. The use of <em>m</em>-CPBA as the oxidant allows the oxidation of iodobenzene to a hypervalent iodine species, driving the catalytic cycle. The method features mild reaction conditions, broad scope of heteroarenes and alcohols, and scaled up preparations. This approach provides a notable supplement to iodobenzene-catalyzed ionic reactions, and opens up a new avenue for its application in radical chemistry.</p></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"4 ","pages":"Article 100031"},"PeriodicalIF":0.0000,"publicationDate":"2022-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666951X22000274/pdfft?md5=60b53769fdcf86f10b9d608205504689&pid=1-s2.0-S2666951X22000274-main.pdf","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron chem","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S2666951X22000274","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
A Minisci-type reaction catalyzed by iodobenzene is disclosed here for the first time. The heteroarylation of unprotected aliphatic alcohols proceeds via alkoxy radical-induced homolytic cleavage of C–H and C–C bonds under photochemical conditions. The use of m-CPBA as the oxidant allows the oxidation of iodobenzene to a hypervalent iodine species, driving the catalytic cycle. The method features mild reaction conditions, broad scope of heteroarenes and alcohols, and scaled up preparations. This approach provides a notable supplement to iodobenzene-catalyzed ionic reactions, and opens up a new avenue for its application in radical chemistry.
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