Organocatalytic Arylation of α-Ketoesters Based on Umpolung Strategy: Phosphazene-Catalyzed SNAr Reaction Utilizing [1,2]-Phospha-Brook Rearrangement

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11 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)13110-13113
Number of pages4
JournalChemistry - A European Journal
Volume24
Issue number50
DOIs
Publication statusPublished - 2018 Sep 6

Keywords

  • SAr reaction
  • [1,2]-phospha-Brook rearrangement
  • base catalysis
  • organocatalysts
  • umpolung

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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