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

Dallas, A. S.; Gothelf, K. V.

J. Org. Chem. 2005, 70, 3321–3323, doi: 10.1021/jo050017

Interdisciplinary Nanoscience Center (iNANO) and Center for Catalysis, Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus C, Denmark.

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.

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