Effect of water on the palladium-catalyzed amidation of aryl bromides

J Org Chem. 2005 Apr 15;70(8):3321-3. doi: 10.1021/jo0500176.

Abstract

The presence of water was found to have a significant impact on the conversion of some Hartwig-Buchwald reactions between amides with arylbromides. Seven amidation reactions were studied in a series of experiments containing 0-400 mol % water. When cesium carbonate is used as the base both in dioxane and toluene, water can have a beneficial effect. The experiments have also shown that for some reactions, anhydrous conditions are unnecessary and sometimes can hinder the reaction.