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Effect of Water on the Palladium-Catalyzed Amidation of Aryl Bromides

2005; American Chemical Society; Volume: 70; Issue: 8 Linguagem: Inglês

10.1021/jo0500176

1520-6904

Andrea Dallas, Kurt V. Gothelf,

Advanced Synthetic Organic Chemistry

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.