Synthesis of trifluoromethyl ketones by palladium-catalyzed cross-coupling reaction of phenyl trifluoroacetate with organoboron compounds

R. Kakino, I. Shimizu, A. Yamamoto

Research output: Contribution to journalArticle

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Abstract

Cross-coupling reaction of aryl trifluoroacetates with organoboron compounds catalyzed by palladium complexes gives trifluoromethyl ketones in moderate to excellent yields under mild conditions. The catalytic process has been designed on the basis of fundamental studies dealing with oxidative addition of phenyl trifluoroacetate to a Pd(0) complex to give a (phenoxo)(trifluoroacetyl)palladium(II) complex and its subsequent reaction with phenylboronic acid to liberate phenyl trifluoromethyl ketone. The catalytic cycle is proposed to be composed of (a) oxidative addition of the ester to give acyl(aryloxo)palladium intermediate, (b) the subsequent transmetallation with arylboron compounds, and (c) reductive elimination. Palladium(0) complexes, as well as catalysts prepared in situ from palladium acetate and 3 molar amounts of tributylphosphine or phosphite at room temperature, serve as convenient and effective catalysts. The process is applicable to a wide range of phenyl- and naphthylboronic acids to give various aryl trifluoromethyl ketones under mild conditions. Aryl perfluoroalkyl ketone derivatives can be similarly prepared in high yields from various phenyl perfluoroalkanecarboxylates and arylboronic acids.

Original languageEnglish
Pages (from-to)371-376
Number of pages6
JournalBulletin of the Chemical Society of Japan
Volume74
Issue number2
DOIs
Publication statusPublished - 2001 Feb

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Trifluoroacetic Acid
Palladium
Ketones
Phosphites
Catalysts
Acids
Esters
Acetates
Derivatives

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Synthesis of trifluoromethyl ketones by palladium-catalyzed cross-coupling reaction of phenyl trifluoroacetate with organoboron compounds. / Kakino, R.; Shimizu, I.; Yamamoto, A.

In: Bulletin of the Chemical Society of Japan, Vol. 74, No. 2, 02.2001, p. 371-376.

Research output: Contribution to journalArticle

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