Palladium-catalyzed alkenylation via sp2 C-H bond activation using phenolic hydroxyl as the directing group

J Org Chem. 2014 Apr 4;79(7):3200-5. doi: 10.1021/jo4028825. Epub 2014 Mar 20.

Abstract

This note describes the efficient and highly regioselective synthesis of 2-(2'-alkenylphenyl)phenol derivatives via palladium-catalyzed 2'-alkenylation of 2-arylphenols directed by the phenolic hydroxyl group using benzoquinone as the oxidant in an atmosphere of air. This reaction can tolerate a series of functional groups and provides the alkenylation products regio- and stereoselectively in moderate to good yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Benzoquinones / chemistry*
  • Catalysis
  • Hydrogen Bonding
  • Palladium / chemistry*
  • Phenols / chemistry*
  • Stereoisomerism

Substances

  • Alkenes
  • Benzoquinones
  • Phenols
  • Palladium