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Highly efficient amine‐based catalytic system for room temperature Suzuki–Miyaura reactions of aryl halides with arylboronic acids
Author(s) -
Das Pankaj,
Sarmah Chandan,
Tairai Archana,
Bora Utpal
Publication year - 2011
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.1755
Subject(s) - chemistry , yield (engineering) , aryl , halide , amine gas treating , catalysis , ligand (biochemistry) , medicinal chemistry , coupling reaction , organic chemistry , polymer chemistry , combinatorial chemistry , alkyl , biochemistry , materials science , receptor , metallurgy
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.