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- Title
Organocatalytic Arylation of α‐Ketoesters Based on Umpolung Strategy: Phosphazene‐Catalyzed S<sub>N</sub>Ar Reaction Utilizing [1,2]‐Phospha‐Brook Rearrangement.
- Authors
Kondoh, Azusa; Aoki, Takuma; Terada, Masahiro
- Abstract
Abstract: An organocatalytic arylation of α‐ketoesters was developed on the basis of umpolung strategy. Phosphazene P2‐tBu efficiently catalyzes the three‐component coupling reaction of α‐ketoesters, a silylated secondary phosphite, and electron‐deficient fluoroarenes to provide α‐hydroxyester derivatives possessing an electron‐deficient aryl group at the α‐position. The reaction involves the catalytic generation of α‐oxygenated ester enolates from α‐ketoesters through the [1,2]‐phospha‐Brook rearrangement followed by the SNAr reaction.
- Subjects
ORGANOCATALYSIS; ARYLATION kinetics; KETONIC acids; PHOSPHAZENES; ELECTRON-deficient compounds; COUPLING reactions (Chemistry)
- Publication
Chemistry - A European Journal, 2018, Vol 24, Issue 50, p13110
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201803218