A palladium-catalyzed carbonylation approach to acid chloride synthesis

J Am Chem Soc. 2013 Nov 13;135(45):16841-4. doi: 10.1021/ja4098093. Epub 2013 Oct 29.

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(t)Bu3) and CO coordination has been found to facilitate the rapid carbonylation of aryl iodides into acid chlorides via reductive elimination from ((t)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.