{"title":"Heteroaryl-Directed Iridium-Catalyzed Enantioselective C–H Alkenylations of Secondary Alcohols","authors":"Wenbin Mao, Craig M. Robertson, John F. Bower","doi":"10.1021/jacs.4c16414","DOIUrl":null,"url":null,"abstract":"Under iridium-catalyzed conditions, 2-aza-aryl-substituted secondary alcohols undergo C(sp<sup>3</sup>)–H addition reactions to alkynes to provide alkenylated tertiary alcohols. The processes occur with very high regio- and enantioselectivity. An analogous addition to styrene is shown to provide a prototype C(sp<sup>3</sup>)–H alkylation process. A mechanism based on directed aza-enolization of the reactant alcohol is proposed.","PeriodicalId":49,"journal":{"name":"Journal of the American Chemical Society","volume":"28 1","pages":""},"PeriodicalIF":14.4000,"publicationDate":"2024-12-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of the American Chemical Society","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/jacs.4c16414","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
Under iridium-catalyzed conditions, 2-aza-aryl-substituted secondary alcohols undergo C(sp3)–H addition reactions to alkynes to provide alkenylated tertiary alcohols. The processes occur with very high regio- and enantioselectivity. An analogous addition to styrene is shown to provide a prototype C(sp3)–H alkylation process. A mechanism based on directed aza-enolization of the reactant alcohol is proposed.
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The flagship journal of the American Chemical Society, known as the Journal of the American Chemical Society (JACS), has been a prestigious publication since its establishment in 1879. It holds a preeminent position in the field of chemistry and related interdisciplinary sciences. JACS is committed to disseminating cutting-edge research papers, covering a wide range of topics, and encompasses approximately 19,000 pages of Articles, Communications, and Perspectives annually. With a weekly publication frequency, JACS plays a vital role in advancing the field of chemistry by providing essential research.
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