期刊
ORGANIC & BIOMOLECULAR CHEMISTRY
卷 17, 期 3, 页码 482-489出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c8ob01811a
关键词
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资金
- Spanish Ministerio de Economia y Competitividad (MINECO) [CTQ2013-43446-P, CTQ2014-51912-REDC]
- Spanish Ministerio de Economia, Industria y Competitividad, Agencia Estatal de Investigacion (AEI)
- Fondo Europeo de Desarrollo Regional (FEDER, EU) [CTQ2016-76782-P, CTQ2016-81797-REDC]
- Generalitat Valenciana [PROMETEOII/2014/017]
- University of Alicante
- MINECO
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.
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