Synthesis of α-fluoroketones based on palladium-catalyzed Decarboxylation reactions of allyl β-keto carboxylates

Isao Shimizu, Hirotoshi Ishii

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

Fluorination of allyl β-keto carboxylates using N-fluoro-2,4,6-pyridinium triflate gave allyl α-fluoro-β-keto carboxylates. Reaction of allyl α-fluoro-β-keto carboxylates with formic acid in the presence of palladium-phosphine catalyst gave α-fluoro ketones. When the palladium-catalyzed reaction was carried out without formic acid, the decarboxylation-allylation took place to give α-fluoro-allylketones. Decarboxylation-dehydrogenation to afford α-fluoro-α,β-unsaturated ketones was carried out with palladium catalysts in acetonitrile.

Original languageEnglish
Pages (from-to)487-495
Number of pages9
JournalTetrahedron
Volume50
Issue number2
DOIs
Publication statusPublished - 1991

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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