Simple, chemoselective hydrogenation with thermodynamic stereocontrol

J Am Chem Soc. 2014 Jan 29;136(4):1300-3. doi: 10.1021/ja412342g. Epub 2014 Jan 15.

Abstract

Few methods permit the hydrogenation of alkenes to a thermodynamically favored configuration when steric effects dictate the alternative trajectory of hydrogen delivery. Dissolving metal reduction achieves this control, but with extremely low functional group tolerance. Here we demonstrate a catalytic hydrogenation of alkenes that affords the thermodynamic alkane products with remarkably broad functional group compatibility and rapid reaction rates at standard temperature and pressure.

Publication types

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

MeSH terms

  • Alkanes / chemical synthesis*
  • Alkanes / chemistry
  • Alkenes / chemistry*
  • Catalysis
  • Hydrogen / chemistry
  • Hydrogenation
  • Molecular Structure
  • Stereoisomerism
  • Thermodynamics*

Substances

  • Alkanes
  • Alkenes
  • Hydrogen