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4‐Aryl‐2‐quinolones through a Pseudo‐Domino Heck/Buchwald–Hartwig Reaction in a Molten Tetrabutylammonium Acetate/ Tetrabutylammonium Bromide Mixture
Author(s) -
Battistuzzi Gianfranco,
Bernini Roberta,
Cacchi Sandro,
De Salve Ilse,
Fabrizi Giancarlo
Publication year - 2007
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200600342
Subject(s) - chemistry , aryl , heck reaction , intramolecular force , domino , ammonium acetate , medicinal chemistry , bromide , phosphine , palladium , organic chemistry , catalysis , cascade reaction , alkyl , high performance liquid chromatography
4‐Aryl‐2‐quinolones can be prepared from readily available o ‐bromocinnamamide and aryl iodides using phosphine‐free palladium( II ) acetate as the precatalyst and a molten tetra( n ‐butyl)ammonium acetate/tetra( n ‐butyl)ammonium bromide mixture as the reaction medium. The reaction proceeds through a pseudo‐domino process involving two mechanistically independent, sequential catalytic cycles: a Heck reaction followed by an intramolecular Buchwald–Hartwig CN bond forming reaction.