Jump to main content
Jump to site search

Issue 3, 2019
Previous Article Next Article

Synthesis of 3-substituted 3-fluoro-2-oxindoles by deacylative alkylation

Author affiliations

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

Back to tab navigation

Supplementary files

Article information


Submitted
27 Jul 2018
Accepted
10 Dec 2018
First published
10 Dec 2018

Org. Biomol. Chem., 2019,17, 482-489
Article type
Paper

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

Social activity

Search articles by author

Spotlight

Advertisements