[Pd]-Catalyzed para-selective allylation of phenols: access to 4-[(E)-3-aryl/alkylprop-2-enyl]phenols

Org Biomol Chem. 2021 Oct 6;19(38):8259-8263. doi: 10.1039/d1ob01489g.

Abstract

4-[(E)-3-Arylprop-2-enyl]phenols are omnipresent scaffolds and constitute natural products and biologically significant compounds. Obtusastyrene and obtustyrene are two such phenolic-based natural products isolated from Dalbergia retusa. The development of strategies based on a site-selective allylation, particularly protecting group-free substrates and non-activated coupling agents, is indispensable in organic synthesis. Herein, we present a highly regioselective [Pd]-catalyzed para-allylation of phenols using simple, inactivated allylic alcohols as allylating coupling partners. Notably, this strategy is successful in open-air and under mild reaction conditions. Besides, the efficacy of the present protocol was demonstrated by the direct synthesis of obtusastyrene and obtustyrene.

Publication types

  • Research Support, Non-U.S. Gov't
  • Comment

MeSH terms

  • Catalysis
  • Molecular Structure
  • Phenols* / chemistry

Substances

  • Phenols