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

R. Kakino, I. Shimizu, A. Yamamoto*

*この研究の対応する著者

研究成果: Article査読

128 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)371-376
ページ数6
ジャーナルBulletin of the Chemical Society of Japan
74
2
DOI
出版ステータスPublished - 2001 2月

ASJC Scopus subject areas

  • 化学 (全般)

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