A Palladium-Catalyzed Carbonylation Approach to Acid Chloride Synthesis

Abstract

We describe a new approach to acid chloride synthesis via the palladium-catalyzed carbonylation of aryl iodides. The combination of sterically encumbered phosphines (P^<i>t</i>Bu₃) and CO coordination has been found to facilitate the rapid carbonylation of aryl iodides into acid chlorides via reductive elimination from (^<i>t</i>Bu₃P)­(CO)­Pd­(COAr)­Cl. The formation of acid chlorides can also be exploited to perform traditional aminocarbonylation reactions under exceptionally mild conditions (ambient temperature and pressure), and with a range of weakly nucleophilic substrates