Ruthenium-catalyzed C-C coupling of fluorinated alcohols with allenes: dehydrogenation at the energetic limit of β-hydride elimination

Angew Chem Int Ed Engl. 2015 Apr 27;54(18):5465-9. doi: 10.1002/anie.201500238. Epub 2015 Mar 10.

Abstract

Ruthenium(II) complexes catalyze the CC coupling of 1,1-disubstituted allenes and fluorinated alcohols to form homoallylic alcohols bearing all-carbon quaternary centers with good to complete levels of diastereoselectivity. Whereas fluorinated alcohols are relatively abundant and tractable, the corresponding aldehydes are often not commercially available because of their instability.

Keywords: allylic compounds; diastereoselectivity; fluorine; hydrogenation; ruthenium.

Publication types

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

MeSH terms

  • Alkadienes / chemistry*
  • Carbon / chemistry*
  • Catalysis
  • Hydrocarbons, Fluorinated / chemical synthesis*
  • Hydrocarbons, Fluorinated / chemistry
  • Hydrogen / chemistry*
  • Hydrogenation
  • Molecular Structure
  • Oxidation-Reduction
  • Propanols / chemical synthesis*
  • Propanols / chemistry
  • Ruthenium / chemistry*
  • Stereoisomerism

Substances

  • Alkadienes
  • Hydrocarbons, Fluorinated
  • Propanols
  • allyl alcohol
  • Carbon
  • Ruthenium
  • Hydrogen