Pierre Milcendeau, Pierre Colonna, Mohammed Ramdani, Sébastien Garcia-Argote, Nicolas Glinsky-Olivier, Grégory Pieters, Xavier Guinchard
{"title":"Au(I)-Catalyzed Regioselective Hydrogen Isotope Labeling of Indoles","authors":"Pierre Milcendeau, Pierre Colonna, Mohammed Ramdani, Sébastien Garcia-Argote, Nicolas Glinsky-Olivier, Grégory Pieters, Xavier Guinchard","doi":"10.1021/acs.orglett.4c03597","DOIUrl":null,"url":null,"abstract":"The gold(I)-catalyzed hydrogen isotope exchange reaction on indoles and related heterocycles is described under mild conditions and low catalyst loadings, using CD<sub>3</sub>OD and D<sub>2</sub>O as readily available deuterium sources. C3-unsubstituted indoles are labeled at the C3 position with exquisite regioselectivity, while C3-substituted indoles are labeled at the C2 position. The method is also applicable to the regioselective tritiation of indoles. Mechanistic studies revealed the involvement of aurated indoles as key intermediates.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9000,"publicationDate":"2024-11-05","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.4c03597","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
The gold(I)-catalyzed hydrogen isotope exchange reaction on indoles and related heterocycles is described under mild conditions and low catalyst loadings, using CD3OD and D2O as readily available deuterium sources. C3-unsubstituted indoles are labeled at the C3 position with exquisite regioselectivity, while C3-substituted indoles are labeled at the C2 position. The method is also applicable to the regioselective tritiation of indoles. Mechanistic studies revealed the involvement of aurated indoles as key intermediates.
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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