A Domino Oxidation/Arylation/Protodecarboxylation Reaction of Salicylaldehydes: Expanded Access to meta-Arylphenols

Chem Asian J. 2016 Feb 4;11(3):347-50. doi: 10.1002/asia.201500506. Epub 2015 Jun 25.

Abstract

A method that allows salicylaldehydes to be efficiently transformed into meta-arylated phenol derivatives through a cascade oxidation/arylation/protodecarboxylation sequence is presented. We demonstrate that the aldehyde functional group can be used as a convenient removable directing group to control site selectivity in C-H activation. Aldehydes are easily introduced into the starting materials and the group is readily cleaved after the C-H functionalization event.

Keywords: C−H activation; arylation; meta-selective; phenols; salicylaldehydes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Carbon / chemistry
  • Catalysis
  • Hydrogen / chemistry
  • Oxidation-Reduction
  • Phenols / chemistry*
  • Transition Elements / chemistry*
  • Ultraviolet Rays

Substances

  • Aldehydes
  • Phenols
  • Transition Elements
  • salicylaldehyde
  • Carbon
  • Hydrogen