Direct observation of the oxidative addition of the aryl carbon-oxygen bond to a ruthenium complex and consideration of the relative reactivity between aryl carbon-oxygen and aryl carbon-hydrogen bonds

Satoshi Ueno; Eiichiro Mizushima; Naoto Chatani; Fumitoshi Kakiuchi

doi:10.1021/ja067612p

Direct observation of the oxidative addition of the aryl carbon-oxygen bond to a ruthenium complex and consideration of the relative reactivity between aryl carbon-oxygen and aryl carbon-hydrogen bonds

Satoshi Ueno, Eiichiro Mizushima, Naoto Chatani, Fumitoshi Kakiuchi

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

153 Citations (Scopus)

Abstract

When RuH₂(CO)(PPh₃₎₃ was reacted with 2,2-dimethyl-1-(2-p-tolylphenyl)propan-1-one (2), the ruthenium-aryloxy complex 3 was obtained in 76% yield. The structure of this complex was determined from ¹H and ³¹P NMR and X-ray data. Complex 3 showed the catalytic activity for the coupling of 2 with the phenylboronate 4. The ¹H and ³¹P NMR studies of the reaction of Ru(CO)(PPh₃)₃ with o-aryloxy pivalophenone revealed that the C-H bond cleavage is a kinetically favorable process but the C-O bond cleavage is a thermodynamic one. The reaction of 2-methoxyacetophenone with vinylsilane and organoboronate resulted in chemoselective C-C bond formation.

Original language	English
Pages (from-to)	16516-16517
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	128
Issue number	51
DOIs	https://doi.org/10.1021/ja067612p
Publication status	Published - 2006 Dec 27

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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Direct observation of the oxidative addition of the aryl carbon-oxygen bond to a ruthenium complex and consideration of the relative reactivity between aryl carbon-oxygen and aryl carbon-hydrogen bonds. / Ueno, Satoshi; Mizushima, Eiichiro; Chatani, Naoto et al.

In: Journal of the American Chemical Society, Vol. 128, No. 51, 27.12.2006, p. 16516-16517.

Research output: Contribution to journal › Article › peer-review

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abstract = "When RuH2(CO)(PPh3)3 was reacted with 2,2-dimethyl-1-(2-p-tolylphenyl)propan-1-one (2), the ruthenium-aryloxy complex 3 was obtained in 76% yield. The structure of this complex was determined from 1H and 31P NMR and X-ray data. Complex 3 showed the catalytic activity for the coupling of 2 with the phenylboronate 4. The 1H and 31P NMR studies of the reaction of Ru(CO)(PPh3)3 with o-aryloxy pivalophenone revealed that the C-H bond cleavage is a kinetically favorable process but the C-O bond cleavage is a thermodynamic one. The reaction of 2-methoxyacetophenone with vinylsilane and organoboronate resulted in chemoselective C-C bond formation.",

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AU - Ueno, Satoshi

AU - Mizushima, Eiichiro

AU - Chatani, Naoto

AU - Kakiuchi, Fumitoshi

PY - 2006/12/27

Y1 - 2006/12/27

N2 - When RuH2(CO)(PPh3)3 was reacted with 2,2-dimethyl-1-(2-p-tolylphenyl)propan-1-one (2), the ruthenium-aryloxy complex 3 was obtained in 76% yield. The structure of this complex was determined from 1H and 31P NMR and X-ray data. Complex 3 showed the catalytic activity for the coupling of 2 with the phenylboronate 4. The 1H and 31P NMR studies of the reaction of Ru(CO)(PPh3)3 with o-aryloxy pivalophenone revealed that the C-H bond cleavage is a kinetically favorable process but the C-O bond cleavage is a thermodynamic one. The reaction of 2-methoxyacetophenone with vinylsilane and organoboronate resulted in chemoselective C-C bond formation.

AB - When RuH2(CO)(PPh3)3 was reacted with 2,2-dimethyl-1-(2-p-tolylphenyl)propan-1-one (2), the ruthenium-aryloxy complex 3 was obtained in 76% yield. The structure of this complex was determined from 1H and 31P NMR and X-ray data. Complex 3 showed the catalytic activity for the coupling of 2 with the phenylboronate 4. The 1H and 31P NMR studies of the reaction of Ru(CO)(PPh3)3 with o-aryloxy pivalophenone revealed that the C-H bond cleavage is a kinetically favorable process but the C-O bond cleavage is a thermodynamic one. The reaction of 2-methoxyacetophenone with vinylsilane and organoboronate resulted in chemoselective C-C bond formation.

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Direct observation of the oxidative addition of the aryl carbon-oxygen bond to a ruthenium complex and consideration of the relative reactivity between aryl carbon-oxygen and aryl carbon-hydrogen bonds

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