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Organocatalytic Arylation of α‐Ketoesters Based on Umpolung Strategy: Phosphazene‐Catalyzed S N Ar Reaction Utilizing [1,2]‐Phospha‐Brook Rearrangement
Author(s) -
Kondoh Azusa,
Aoki Takuma,
Terada Masahiro
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201803218
Subject(s) - umpolung , phosphazene , chemistry , catalysis , organocatalysis , aryl , medicinal chemistry , combinatorial chemistry , organic chemistry , enantioselective synthesis , alkyl , nucleophile , polymer
Abstract An organocatalytic arylation of α‐ketoesters was developed on the basis of umpolung strategy. Phosphazene P2‐ t Bu 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 S N Ar reaction.