Ruthenium(0)-Catalyzed C-C Coupling of Alkynes and 3-Hydroxy-2-oxindoles: Direct C-H Vinylation of Alcohols

Org Lett. 2017 Feb 17;19(4):966-968. doi: 10.1021/acs.orglett.7b00174. Epub 2017 Feb 6.

Abstract

Upon exposure to a ruthenium(0) catalyst, N-benzyl-3-hydroxy-2-oxindoles react with diverse alkynes to form products of C-H vinylation with complete control of regioselectivity and olefin geometry. This method contributes to a growing body of catalytic processes that enable direct conversion of lower alcohols to higher alcohols in the absence of stoichiometric organometallic reagents.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemistry*
  • Alkenes / chemistry
  • Alkynes / chemistry*
  • Catalysis
  • Coordination Complexes / chemistry*
  • Hydrogenation
  • Ligands
  • Molecular Structure
  • Oxidation-Reduction
  • Oxindoles / chemistry*
  • Ruthenium / chemistry*
  • Stereoisomerism
  • Temperature

Substances

  • Alcohols
  • Alkenes
  • Alkynes
  • Coordination Complexes
  • Ligands
  • Oxindoles
  • 2-oxindole
  • Ruthenium