A ruthenium-catalyzed reaction of aromatic ketones with arylboronates

A new method for the arylation of aromatic compounds via C-H bond cleavage

Fumitoshi Kakiuchi, Shintaro Kan, Kimitaka Igi, Naoto Chatani, Shinji Murai

Research output: Contribution to journalArticle

304 Citations (Scopus)

Abstract

The ruthenium-catalyzed reaction of aromatic ketones with arylboronic acid esters (arylboronates) gave the ortho arylation product. For this coupling reaction, a RuH2(CO)(PPh3)3 complex exhibited the highest catalytic activity among the complexes screened. Several aromatic ketones, for example, acetophenones, acetonaphthone, α-tetralone, and benzosuberone, can be used in this coupling reaction. A variety of arylboronates containing electron-donating (OMe and NMe2) and -withdrawing (F and CF3) groups were found to react with aromatic ketones to give the corresponding aylation products. The corresponding arylboronic acids could be used in this coupling reaction, but the yields were slightly lower, as compared to those of the reaction using the corresponding arylboronates.

Original languageEnglish
Pages (from-to)1698-1699
Number of pages2
JournalJournal of the American Chemical Society
Volume125
Issue number7
DOIs
Publication statusPublished - 2003 Feb 15
Externally publishedYes

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Ruthenium
Aromatic compounds
Ketones
Esters
Acids
Acetophenones
Tetralones
Carbon Monoxide
Catalyst activity
Electrons

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

A ruthenium-catalyzed reaction of aromatic ketones with arylboronates : A new method for the arylation of aromatic compounds via C-H bond cleavage. / Kakiuchi, Fumitoshi; Kan, Shintaro; Igi, Kimitaka; Chatani, Naoto; Murai, Shinji.

In: Journal of the American Chemical Society, Vol. 125, No. 7, 15.02.2003, p. 1698-1699.

Research output: Contribution to journalArticle

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