{"title":"C3 versus C5 Regioselectivity in the Intramolecular Dehydrative Friedel–Crafts Alkylation of Indole C4-Tethered Carbinols","authors":"Abhijit Gogoi, Raju Chouhan, Sajal Kumar Das","doi":"10.1021/acs.orglett.5c00420","DOIUrl":null,"url":null,"abstract":"Described herein is a mild catalytic dehydrative Friedel–Crafts alkylation of 1,1-diarylalkanols─a challenging reaction with exceedingly rare previous success, presumably because of the unfavorable steric hindrance around the reactive centers and the competitive E1 reaction. Executing in an intramolecular fashion and benefiting from the high nucleophilicity of indole, we have successfully utilized this reaction in synthesizing 3,4-fused indoles. Interestingly, the Friedel–Crafts alkylation strategy could also be applied to access 4,5-fused indoles via modification of the tether connecting the alcohol and indole moieties.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"52 1","pages":""},"PeriodicalIF":5.0000,"publicationDate":"2025-03-03","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.5c00420","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
Described herein is a mild catalytic dehydrative Friedel–Crafts alkylation of 1,1-diarylalkanols─a challenging reaction with exceedingly rare previous success, presumably because of the unfavorable steric hindrance around the reactive centers and the competitive E1 reaction. Executing in an intramolecular fashion and benefiting from the high nucleophilicity of indole, we have successfully utilized this reaction in synthesizing 3,4-fused indoles. Interestingly, the Friedel–Crafts alkylation strategy could also be applied to access 4,5-fused indoles via modification of the tether connecting the alcohol and indole moieties.
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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