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

Fingerprint

formic acid
Decarboxylation
Palladium
phosphine
Ketones
Allylation
Fluorination
Catalysts
Halogenation
Dehydrogenation

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis of α-fluoroketones based on palladium-catalyzed Decarboxylation reactions of allyl β-keto carboxylates. / Shimizu, Isao; Ishii, Hirotoshi.

In: Tetrahedron, Vol. 50, No. 2, 1991, p. 487-495.

Research output: Contribution to journalArticle

@article{65cc9fdb477b4dcaa74c893df9046854,
title = "Synthesis of α-fluoroketones based on palladium-catalyzed Decarboxylation reactions of allyl β-keto carboxylates",
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.",
author = "Isao Shimizu and Hirotoshi Ishii",
year = "1991",
doi = "10.1016/S0040-4020(01)80770-5",
language = "English",
volume = "50",
pages = "487--495",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "2",

}

TY - JOUR

T1 - Synthesis of α-fluoroketones based on palladium-catalyzed Decarboxylation reactions of allyl β-keto carboxylates

AU - Shimizu, Isao

AU - Ishii, Hirotoshi

PY - 1991

Y1 - 1991

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=0028091316&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0028091316&partnerID=8YFLogxK

U2 - 10.1016/S0040-4020(01)80770-5

DO - 10.1016/S0040-4020(01)80770-5

M3 - Article

VL - 50

SP - 487

EP - 495

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 2

ER -