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

176 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 languageEnglish
Pages (from-to)2706-2707
Number of pages2
JournalJournal of the American Chemical Society
Volume126
Issue number9
DOIs
Publication statusPublished - 2004 Mar 10
Externally publishedYes

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Ethers
Ruthenium
Ketones
Carbon
Oxygen
Coordination Complexes
Carbon Monoxide
Metal complexes
Ether
Transition metals
Electrons

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Ruthenium-Catalyzed Functionalization of Aryl Carbon-Oxygen Bonds in Aromatic Ethers with Organoboron Compounds. / Kakiuchi, Fumitoshi; Usui, Mayumi; Ueno, Satoshi; Chatani, Naoto; Murai, Shinji.

In: Journal of the American Chemical Society, Vol. 126, No. 9, 10.03.2004, p. 2706-2707.

Research output: Contribution to journal › Article

Kakiuchi, F, Usui, M, Ueno, S, Chatani, N & Murai, S 2004, 'Ruthenium-Catalyzed Functionalization of Aryl Carbon-Oxygen Bonds in Aromatic Ethers with Organoboron Compounds', Journal of the American Chemical Society, vol. 126, no. 9, pp. 2706-2707. https://doi.org/10.1021/ja0393170
Kakiuchi F, Usui M, Ueno S, Chatani N, Murai S. Ruthenium-Catalyzed Functionalization of Aryl Carbon-Oxygen Bonds in Aromatic Ethers with Organoboron Compounds. Journal of the American Chemical Society. 2004 Mar 10;126(9):2706-2707. https://doi.org/10.1021/ja0393170
Kakiuchi, Fumitoshi ; Usui, Mayumi ; Ueno, Satoshi ; Chatani, Naoto ; Murai, Shinji. / Ruthenium-Catalyzed Functionalization of Aryl Carbon-Oxygen Bonds in Aromatic Ethers with Organoboron Compounds. In: Journal of the American Chemical Society. 2004 ; Vol. 126, No. 9. pp. 2706-2707.
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