Ruthenium-catalyzed conversion of sp3 C-O bonds in ethers to C-C bonds using triarylboroxines

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Abstract

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.

Original languageEnglish
Pages (from-to)3254-3257
Number of pages4
JournalOrganic Letters
Volume13
Issue number12
DOIs
Publication statusPublished - 2011 Jun 17

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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