Regioselective Gold-Catalyzed Hydration of CF3- and SF5‑alkynes

Regioselective Gold-Catalyzed Hydration of CF3- and SF5‑alkynes

The regioselective gold-catalyzed hydration of CF3- and SF5-alkynes is described. The corresponding trifluoromethylated and pentasulfanylated ketones are obtained in up to 91% yield as single regioisomers showcasing the use of CF3 and SF5 as highly efficient directing groups in this reaction. Notabl...

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Bibliographic Details
Published in:Organic letters Vol. 21; no. 10; pp. 3866 - 3870
Main Authors: Cloutier, Mélissa, Roudias, Majdouline, Paquin, Jean-François
Format: Journal Article
Language:English
Published: American Chemical Society 17-05-2019
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Summary:The regioselective gold-catalyzed hydration of CF3- and SF5-alkynes is described. The corresponding trifluoromethylated and pentasulfanylated ketones are obtained in up to 91% yield as single regioisomers showcasing the use of CF3 and SF5 as highly efficient directing groups in this reaction. Notably, this transformation represents the first use of CF3- and SF5-alkynes in gold catalysis.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b01379