Tandem ring-closing metathesis/transfer hydrogenation: practical chemoselective hydrogenation of alkenes

Org Lett. 2014 Sep 5;16(17):4444-7. doi: 10.1021/ol5019739. Epub 2014 Aug 20.

Abstract

An operationally simple chemoselective transfer hydrogenation of alkenes using ruthenium metathesis catalysts is presented. Of great practicality, the transfer hydrogenation reagents can be added directly to a metathesis reaction and effect hydrogenation of the product alkene in a single pot at ambient temperature without the need to seal the vessel to prevent hydrogen gas escape. The reduction is applicable to a range of alkenes and can be performed in the presence of aryl halides and benzyl groups, a notable weakness of Pd-catalyzed hydrogenations. Scope and mechanistic considerations are presented.

MeSH terms

  • Alkenes / chemistry*
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Cyclization
  • Hydrogenation
  • Molecular Structure
  • Ruthenium / chemistry

Substances

  • Alkenes
  • Ruthenium