Highly efficient amine-based catalytic system for room temperature Suzuki-Miyaura reactions of aryl halides with arylboronic acids

摘要

An in situ-generated catalytic system based on PdCI2 and primary amine-based ligand exhibited excellent activity (up to 98% isolated yield) in the Suzuki-Miyaura cross-coupling reactions of aryl bromides with arylboronic acids in water, at room temperature, withoutanyadditive.Theefficienciesoftheligandsfollowtheorder:(C6H5)3CNH2 >C6H5CH2 NH2 >C6H5 NH2 > C6H_(11) NH2, which is in accordance with the palladacycle forming capacity of the respective ligands. Moderate-to-good yields (up to 78% isolated yield) of the coupling products were also obtained with less reactive aryl chlorides as substrates at room temperature in isopropanol using an alternative protocol based on Pd(OAc)2 and (C6H5)3CNH2.