Copper-catalyzed oxidative coupling of formamides with salicylaldehydes: synthesis of carbamates in the presence of a sensitive aldehyde group

J Org Chem. 2014 Apr 4;79(7):3206-14. doi: 10.1021/jo402798k. Epub 2014 Mar 14.

Abstract

A diverse library of novel carbamates was synthesized utilizing copper-catalyzed oxidative C-O coupling of formamides and salicylaldehydes. Sensitive aldehyde groups remained intact in the presence of an oxidant and a transition-metal salt. Salicylaldehydes bearing electron-donating, electron-withdrawing, and halogen groups as well as 1-hydroxy-2-naphthaldehydes provided the desired carbamates in good to excellent yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Carbamates / chemical synthesis*
  • Carbamates / chemistry
  • Catalysis
  • Copper / chemistry*
  • Formamides / chemistry*
  • Molecular Structure
  • Oxidative Coupling

Substances

  • Aldehydes
  • Carbamates
  • Formamides
  • salicylaldehyde
  • Copper