General copper-catalyzed transformations of functional groups from arylboronic acids in water

Article abstract of DOI:10.1002/chem.201003711

A simple and general copper-catalyzed method has been developed for transformations of various functional groups (i I, i N₃, i SO₂R, i OH, i NH₂, and i NO ₂) on aromatic rings from arylboronic acids in water under air. The protocol uses cheap and readily available inorganic salts (KI, NaN₃, NaSO₂R, NaOH, NaNO₂) and aqueous ammonia as the functional-group sources, simple Cu₂O/NH₃ as the catalyst system, environmentally friendly water as the solvent, and oxygen in air as the oxidant. Importantly, the copper catalyst system in water was recyclable. This study should provide a useful strategy for interconversions of the functional groups on aromatic rings.