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Ruthenium-Catalyzed Conversion of sp3 C–O Bonds in Ethers to C–C Bonds Using Triarylboroxines

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journal contribution
posted on 17.06.2011, 00:00 by Yohei Ogiwara, Takuya Kochi, Fumitoshi Kakiuchi
Catalytic conversion of unreactive sp3 C–O bonds in alkyl ethers to C–C bonds is described. Alkyl ethers bearing 2- or 4-pyridyl groups were coupled with triarylboroxines in the presence of a ruthenium catalyst. Triarylboroxines bearing a variety of functional groups including electron-withdrawing and -donating groups can be used for the reaction. No additional base was required for the coupling with the organoboron reagents, and base-sensitive groups can be tolerated. The reaction is considered to proceed via dehydroalkoxylation followed by addition of triarylboroxines to form C–C bonds.