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

An in situ ‐generated catalytic system based on PdCl 2 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, without any additive. The efficiencies of the ligands follow the order: (C 6 H 5 ) 3 CNH 2 > C 6 H 5 CH 2 NH 2 > C 6 H 5 NH 2 > C 6 H 11 NH 2 , 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 (C 6 H 5 ) 3 CNH 2 . Copyright © 2011 John Wiley & Sons, Ltd.