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Very Fast Suzuki–Miyaura Reaction Catalyzed by Pd(OAc) 2 under Aerobic Conditions at Room Temperature in EGME/H 2 O
Author(s) -
Del Zotto Alessandro,
Amoroso Francesco,
Baratta Walter,
Rigo Pierluigi
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800874
Subject(s) - chemistry , bromobenzene , phenylboronic acid , nitrobenzene , catalysis , aryl , medicinal chemistry , ligand (biochemistry) , chloride , ethylene glycol , toluene , coupling reaction , organic chemistry , solvent , alkyl , receptor , biochemistry
The results of a ligand‐free Pd(OAc) 2 ‐catalyzed Suzuki–Miyaura C–C coupling performed at room temperature under aerobic conditions are presented. It was found that the use of an ethylene glycol monomethyl ether/H 2 O mixture as the solvent resulted in very rapid reactions of aryl bromides with arylboronic acids. As a matter of fact, under optimized conditions, some substrates were converted quantitatively in less than 1 min with exceptionally high TOF values. For example, the reaction between 4‐methoxyphenylboronic acid and bromobenzene afforded 4‐methoxybiphenyl in 30 s with TOF = 180000 h –1 . Furthermore, the reaction tolerates a wide range of functional groups and can be successfully applied to heteroaryl bromides such as 2‐bromopyridine and 5‐bromopyrimidine. Interestingly, also an activated aryl chloride such as 1‐chloro‐4‐nitrobenzene reacted quantitatively with phenylboronic acid at 373 K. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)