Pd-catalyzed chemoselective carbonylation of aminophenols with iodoarenes: alkoxycarbonylation vs aminocarbonylation.

Abstract

Palladium-catalyzed chemoselective carbonylation of aminophenols with iodoarenes was realized by changing ligand and base. 3- or 4-Aminophenols afforded esters in high yields and selectivities using 1,3-bis(diphenylphosphino)propane as the ligand and K2CO3 as the base, and gave amides in high yields and selectivities using 1,3-bis(diisobutylphosphino)propane as the ligand and DBU as the base. 2-Aminophenol only gave amides in high yields under both conditions.