Efficient alkyl ether synthesis via palladium-catalyzed, picolinamide-directed alkoxylation of unactivated C(sp 3)-H and C(sp 2)-H bonds at remote positions

Shu Yu Zhang, Gang He, Yingsheng Zhao, Kiwan Wright, William A. Nack, Gong Chen

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Abstract

We report the efficient synthesis of alkyl ethers by the functionalization of unactivated sp 3- and sp 2-hybridized C-H bonds. In the Pd(OAc) 2-catalyzed, PhI(OAc) 2-mediated reaction system, picolinamide-protected amine substrates undergo facile alkoxylation at the γ or δ positions with a range of alcohols, including t-BuOH, to give alkoxylated products. This method features a relatively broad substrate scope for amines and alcohols, inexpensive reagents, and convenient operating conditions. This method highlights the emerging value of unactivated C-H bonds, particularly the C(sp 3)-H bond of methyl groups, as functional groups in organic synthesis.

Original languageEnglish (US)
Pages (from-to)7313-7316
Number of pages4
JournalJournal of the American Chemical Society
Volume134
Issue number17
DOIs
StatePublished - May 2 2012

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All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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