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Issue 3, 2019
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Synthesis of 3-substituted 3-fluoro-2-oxindoles by deacylative alkylation

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Abstract

The fluorination of 3-acetyl-2-oxindoles with N-fluorobenzenesulfonimide under Lewis acid catalysis using Mg(ClO4)2 gives the starting compounds 3-acetyl-3-fluoro-2-oxindoles. These compounds are subjected to base-promoted deacylative alkylation (DaA) for the in situ generation of 3-fluoro-2-oxindole enolates under very mild reaction conditions using Triton B (1 equiv.) and alkyl halides and Michael acceptors as electrophilic reagents. The corresponding 3-alkylated-3-fluoro-2-oxindoles are obtained in good to very high yields. In addition, the palladium-catalyzed deacylative allylation is carried out with allylic alcohols using LiOtBu as the base and 6 mol% of Pd(OAc)2 and dppp, giving the resulting 3-allylated 3-fluoro-2-oxindoles in good yields. This methodology allows a simple synthesis of 3-alkylated-3-fluoro-2-oxindoles, which are difficult to obtain by other routes.

Graphical abstract: Synthesis of 3-substituted 3-fluoro-2-oxindoles by deacylative alkylation

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Publication details

The article was received on 27 Jul 2018, accepted on 10 Dec 2018 and first published on 10 Dec 2018


Article type: Paper
DOI: 10.1039/C8OB01811A
Citation: Org. Biomol. Chem., 2019,17, 482-489
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    Synthesis of 3-substituted 3-fluoro-2-oxindoles by deacylative alkylation

    C. Molina, A. Ortega-Martínez, J. M. Sansano and C. Nájera, Org. Biomol. Chem., 2019, 17, 482
    DOI: 10.1039/C8OB01811A

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