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 PdCl₂ 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: (C₆H₅)₃CNH₂ > C₆H₅CH₂ NH₂ > C₆H₅ NH₂ > C₆H₁₁ 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. Copyright ? 2011 John Wiley & Sons, Ltd.