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Preparation of 2‐Quinolones by Sequential Heck Reduction–Cyclization (HRC) Reactions by Using a Multitask Palladium Catalyst
Author(s) -
Felpin FrançoisXavier,
Coste Jérôme,
Zakri Cécile,
Fouquet Eric
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200900583
Subject(s) - palladium , catalysis , chemistry , electrophile , hydrogenolysis , homogeneous , sequence (biology) , heck reaction , reactivity (psychology) , combinatorial chemistry , ligand (biochemistry) , base (topology) , organic chemistry , medicine , mathematical analysis , biochemistry , physics , alternative medicine , receptor , mathematics , pathology , thermodynamics
One‐pot sequential Heck reduction–cyclization (HRC) reactions leading to the synthesis of substituted 2‐quinolones have been developed by using a heterogeneous or mixed homogeneous/heterogeneous multitask palladium catalyst with charcoal as a support. The whole sequence occurs under very mild conditions without the need for additives (ligand or base) by taking advantage of the high reactivity of aryldiazonium salts as “super electrophiles”. Recycling experiments showed that the reused heterogeneous Pd 0 /C catalyst was not able to promote another HRC sequence but was, however, still highly active for hydrogenation, hydrodehalogenation, as well as hydrogenolysis reactions.