Double arylation of allyl alcohol via a one-pot Heck arylation-isomerization-acylation cascade

Org Lett. 2011 Oct 21;13(20):5456-9. doi: 10.1021/ol202144z. Epub 2011 Sep 20.

Abstract

A one-pot, two-step catalytic protocol has been developed. A regioselective Heck coupling between aryl bromides and allyl alcohol leads to the generation of arylated allyl alcohols that in situ isomerize to give aldehydes, which then undergo an acylation reaction with a second aryl bromide. A variety of aryl bromides can be employed in both the initial Heck reaction and the acylation, providing easy access to a wide variety of substituted dihydrochalcones.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acylation
  • Catalysis
  • Chalcones / chemical synthesis*
  • Chalcones / chemistry
  • Combinatorial Chemistry Techniques
  • Hydrocarbons, Brominated / chemistry*
  • Molecular Structure
  • Palladium / chemistry
  • Propanols / chemistry*
  • Stereoisomerism

Substances

  • Chalcones
  • Hydrocarbons, Brominated
  • Propanols
  • allyl alcohol
  • Palladium
  • dihydrochalcone