Ruthenium-Catalyzed Functionalization of Aryl Carbon-Oxygen Bonds in Aromatic Ethers with Organoboron Compounds

Fumitoshi Kakiuchi; Mayumi Usui; Satoshi Ueno; Naoto Chatani; Shinji Murai

doi:10.1021/ja0393170

Ruthenium-Catalyzed Functionalization of Aryl Carbon-Oxygen Bonds in Aromatic Ethers with Organoboron Compounds

Fumitoshi Kakiuchi, Mayumi Usui, Satoshi Ueno, Naoto Chatani, Shinji Murai

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

192 Citations (Scopus)

Abstract

The ruthenium-catalyzed reaction of aryl ethers having a carbonyl group at the ortho position to the ether group with organoboronates (R?B(OCH₂CMe₂CH₂O), R = aryl, alkenyl, and alkyl) resulted in site-selective C?C bond formation. Among the transition metal complexes screened, the RuH₂(CO)(PPh₃)₃ complex showed the highest activity. Several aromatic ketones having methoxy or phenoxy groups at the ortho position can also be used in this coupling reaction. A variety of arylboronates containing electron-donating (NMe₂, OMe, methyl, and vinyl) and -withdrawing (F and CF₃) groups reacted with methoxy ketones to give the corresponding coupling products in high yields.

Original language	English
Pages (from-to)	2706-2707
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	126
Issue number	9
DOIs	https://doi.org/10.1021/ja0393170
Publication status	Published - 2004 Mar 10
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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title = "Ruthenium-Catalyzed Functionalization of Aryl Carbon-Oxygen Bonds in Aromatic Ethers with Organoboron Compounds",

abstract = "The ruthenium-catalyzed reaction of aryl ethers having a carbonyl group at the ortho position to the ether group with organoboronates (R?B(OCH2CMe2CH2O), R = aryl, alkenyl, and alkyl) resulted in site-selective C?C bond formation. Among the transition metal complexes screened, the RuH2(CO)(PPh3)3 complex showed the highest activity. Several aromatic ketones having methoxy or phenoxy groups at the ortho position can also be used in this coupling reaction. A variety of arylboronates containing electron-donating (NMe2, OMe, methyl, and vinyl) and -withdrawing (F and CF3) groups reacted with methoxy ketones to give the corresponding coupling products in high yields.",

author = "Fumitoshi Kakiuchi and Mayumi Usui and Satoshi Ueno and Naoto Chatani and Shinji Murai",

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T1 - Ruthenium-Catalyzed Functionalization of Aryl Carbon-Oxygen Bonds in Aromatic Ethers with Organoboron Compounds

AU - Kakiuchi, Fumitoshi

AU - Usui, Mayumi

AU - Ueno, Satoshi

AU - Chatani, Naoto

AU - Murai, Shinji

PY - 2004/3/10

Y1 - 2004/3/10

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AB - The ruthenium-catalyzed reaction of aryl ethers having a carbonyl group at the ortho position to the ether group with organoboronates (R?B(OCH2CMe2CH2O), R = aryl, alkenyl, and alkyl) resulted in site-selective C?C bond formation. Among the transition metal complexes screened, the RuH2(CO)(PPh3)3 complex showed the highest activity. Several aromatic ketones having methoxy or phenoxy groups at the ortho position can also be used in this coupling reaction. A variety of arylboronates containing electron-donating (NMe2, OMe, methyl, and vinyl) and -withdrawing (F and CF3) groups reacted with methoxy ketones to give the corresponding coupling products in high yields.

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