{"title":"Regioselective synthesis of 2-aminophenols from N-arylhydroxylamines","authors":"Zhiwei Gao, Zhiguo Hou, Hongyin Gao","doi":"10.1039/d4ob01281j","DOIUrl":null,"url":null,"abstract":"A novel strategy for the synthesis of 2-aminophenols in the absence of metals and oxidants was described. The 2-aminophenols were efficiently obtained through a cascade [3,3]-sigmatropic rearrangement and <em>in situ</em> hydrolysis process by using readily available <em>N</em>-arylhydroxylamines and the <em>in situ</em>-generated methyl chlorosulfonate from commercially available sulfuryl chloride and methanol under mild conditions. This method could be scaled up and has a wide substrate scope with great functional group tolerance and high regioselectivity. The 2-aminophenol products could be readily converted into structurally diverse functional molecules in good yields under various conditions.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9000,"publicationDate":"2024-09-04","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/d4ob01281j","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
A novel strategy for the synthesis of 2-aminophenols in the absence of metals and oxidants was described. The 2-aminophenols were efficiently obtained through a cascade [3,3]-sigmatropic rearrangement and in situ hydrolysis process by using readily available N-arylhydroxylamines and the in situ-generated methyl chlorosulfonate from commercially available sulfuryl chloride and methanol under mild conditions. This method could be scaled up and has a wide substrate scope with great functional group tolerance and high regioselectivity. The 2-aminophenol products could be readily converted into structurally diverse functional molecules in good yields under various conditions.