{"title":"Stereoselective Copper-Catalyzed Cross-Coupling of α-CF<sub>3</sub>-Allylboronic Acids with Diazoketones.","authors":"Tautvydas Kireilis, Kálmán J Szabó","doi":"10.1021/acs.joc.4c02869","DOIUrl":null,"url":null,"abstract":"<p><p>We have studied copper-catalyzed cross-coupling of chiral α-CF<sub>3</sub>-substituted allylboronic acids with α-diazoketones. The reaction proceeds with excellent regioselectivity and stereoselectivity via allylic rearrangement. The method is useful for formation a new allylic C(sp<sup>3</sup>)-C(sp<sup>3</sup>) bond with high selectivity. The poor yield is a limitation of this reaction.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":" ","pages":"2542-2546"},"PeriodicalIF":3.6000,"publicationDate":"2025-02-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11833876/pdf/","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.4c02869","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/1/30 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
We have studied copper-catalyzed cross-coupling of chiral α-CF3-substituted allylboronic acids with α-diazoketones. The reaction proceeds with excellent regioselectivity and stereoselectivity via allylic rearrangement. The method is useful for formation a new allylic C(sp3)-C(sp3) bond with high selectivity. The poor yield is a limitation of this reaction.
期刊介绍：
Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.
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