Gold Activation of Nitriles: Catalytic Hydration to Amides

A gold-based catalytic system that efficiently mediates the hydration of a broad spectrum of nitriles, including aromatic, heteroaromatic and aliphatic examples and efficiently catalyze the hydration of a range of organonitriles has been reported. Nitriles are considered inert in the context gold catalysis and have only been used as reaction solvent or as throw-away ligands in well-defined cationic gold catalysis. The obtained product was purified by flash chromatography using a gradient of pentane/ethyl acetate and compound 1 was isolated as a colorless solid. Aromatic substrates bearing two nitrile groups as in rn-benzenedinitrile and p-benzenedinitrile underwent double nitrile hydration and afforded excellent yields in the corresponding diamides. There is high relevance for the use of cationic gold complexes bearing such ligands and should have important implications in catalysis.