{"title":"Metal-Catalyzed Hydrogen Atom Transfer (MHAT) Hydroalkylation with Electron-Deficient Alkynes.","authors":"Laura G Rodríguez, Josep Bonjoch, Ben Bradshaw","doi":"10.1021/acs.orglett.4c03943","DOIUrl":null,"url":null,"abstract":"<p><p>We present a novel strategy for olefin construction via the reductive coupling of electron-neutral alkenes with electron-deficient alkynes under metal-catalyzed hydrogen atom transfer conditions. This methodology provides selective access to both <i>trans</i> and the more challenging-to-synthesize <i>cis</i> isomers and permits the olefin to be installed next to sterically hindered centers, key factors in the synthesis of biologically active compounds. The reaction exhibits broad functional group tolerance and proceeds under mild, nontoxic conditions with high atom efficiency.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":"10553-10558"},"PeriodicalIF":4.9000,"publicationDate":"2024-12-13","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.4c03943","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/11/28 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
We present a novel strategy for olefin construction via the reductive coupling of electron-neutral alkenes with electron-deficient alkynes under metal-catalyzed hydrogen atom transfer conditions. This methodology provides selective access to both trans and the more challenging-to-synthesize cis isomers and permits the olefin to be installed next to sterically hindered centers, key factors in the synthesis of biologically active compounds. The reaction exhibits broad functional group tolerance and proceeds under mild, nontoxic conditions with high atom efficiency.
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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