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

doi:10.1021/ja029273f

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 journal › Article › peer-review

339 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 language	English
Pages (from-to)	1698-1699
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	125
Issue number	7
DOIs	https://doi.org/10.1021/ja029273f
Publication status	Published - 2003 Feb 15
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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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.",

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T2 - A new method for the arylation of aromatic compounds via C-H bond cleavage

AU - Kakiuchi, Fumitoshi

AU - Kan, Shintaro

AU - Igi, Kimitaka

AU - Chatani, Naoto

AU - Murai, Shinji

PY - 2003/2/15

Y1 - 2003/2/15

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A ruthenium-catalyzed reaction of aromatic ketones with arylboronates: A new method for the arylation of aromatic compounds via C-H bond cleavage

Abstract

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