Pd-catalyzed regioselective allylation of mono- and disubstituted hydrazines

Org Lett. 2013 Jul 5;15(13):3381-3. doi: 10.1021/ol4014798. Epub 2013 Jun 17.

Abstract

Palladium-catalyzed allylation of hydrazines using allyl alcohols is reported. This highly efficient protocol furnishes monoallylated hydrazines selectively, in 27-99% yields. Following an optimization of the reaction conditions and of the Pd-ligands, the allylations of both mono- and disubstituted hydrazines were investigated, as well as the effects of C2-substitution on the allylating agent. Of particular interest, a novel method for the selective monoallylation of monosubstituted hydrazines is demonstrated.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Allyl Compounds / chemistry*
  • Catalysis
  • Hydrazines / chemical synthesis*
  • Hydrazines / chemistry*
  • Ligands
  • Molecular Structure
  • Palladium / chemistry*
  • Propanols / chemistry*
  • Stereoisomerism

Substances

  • Allyl Compounds
  • Hydrazines
  • Ligands
  • Propanols
  • allyl alcohol
  • Palladium