{"title":"Photocatalyst-free regioselective sulfonamidation of <i>N</i>-(2-hydroxyaryl)amides in visible-light.","authors":"Rajat, Shruti Rajput, Nitika Grover, Nidhi Jain","doi":"10.1039/d4ob01393j","DOIUrl":null,"url":null,"abstract":"<p><p>In this work, we report a regioselective sulfonamidation of <i>N</i>-(2-hydroxyaryl)amides with iminoiodinanes and iodine in visible light at room temperature. The method does not require a strong oxidant, metal or photocatalyst and enables direct functionalization of a C-H bond to a C-N bond. Mechanistic investigations suggest <i>in situ</i> generation of an N-centered radical from <i>N</i>,<i>N</i>-diiodo-sulfonamide by homolytic N-I bond cleavage followed by its site-specific addition to <i>N</i>-(2-hydroxyaryl)amides to furnish <i>para</i>-sulfonamide derivatives.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9000,"publicationDate":"2024-10-08","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/d4ob01393j","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
Abstract
In this work, we report a regioselective sulfonamidation of N-(2-hydroxyaryl)amides with iminoiodinanes and iodine in visible light at room temperature. The method does not require a strong oxidant, metal or photocatalyst and enables direct functionalization of a C-H bond to a C-N bond. Mechanistic investigations suggest in situ generation of an N-centered radical from N,N-diiodo-sulfonamide by homolytic N-I bond cleavage followed by its site-specific addition to N-(2-hydroxyaryl)amides to furnish para-sulfonamide derivatives.