{"title":"Synthesis of 2-Arylphenols via Formal Bismuth(V)-Mediated C–O Arylation of Guaiacols","authors":"Natasha F. M. Ansarian, Liam T. Ball","doi":"10.1021/acs.orglett.5c00593","DOIUrl":null,"url":null,"abstract":"We report a new C–O arylation strategy for the synthesis of 2-arylphenols from bio-abundant guaiacols. Functionalization of the strong C–O bond is achieved through a sequence of arylative dearomatization, mediated selectively by an electrophilic bismuth(V) arylating agent, followed by 1,2-reduction and deoxygenative rearomatization. This methodology represents a rare example of complexity-generating deoxygenation applied to lignin-derived biorefinery feedstocks and provides independence from the regioselectivity rules established for the bismuth(V)-mediated arylation of simple phenols.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"52 1","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2025-03-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.5c00593","RegionNum":1,"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
We report a new C–O arylation strategy for the synthesis of 2-arylphenols from bio-abundant guaiacols. Functionalization of the strong C–O bond is achieved through a sequence of arylative dearomatization, mediated selectively by an electrophilic bismuth(V) arylating agent, followed by 1,2-reduction and deoxygenative rearomatization. This methodology represents a rare example of complexity-generating deoxygenation applied to lignin-derived biorefinery feedstocks and provides independence from the regioselectivity rules established for the bismuth(V)-mediated arylation of simple phenols.
期刊介绍：
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
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