Article (Scientific journals)
Versatile synthesis of dissymmetric diarylideneacetones via a palladium-catalyzed coupling-isomerization reaction
Gendron, Thibault; Davioud-Charvet, Elisabeth; Müller, Thomas J. J.
2012In Synthesis, 44 (24), p. 3829 - 3835
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Keywords :
catalysis; cross-coupling; heterocycles; isomerization; palladium; solvent effects; substituent effects; Cross-couplings; Heterocycles; Michael systems; Organic synthesis; Palladium-catalyzed; Reaction conditions; Solvent effects; Substituent effect; Therapeutic Application; Catalysis; Organic Chemistry
Abstract :
[en] As a twofold Michael system, the diarylideneacetone core is of particular interest in organic synthesis and for therapeutic applications. To overcome the drawbacks of the classical Claisen-Schmidt protocol, a new methodology for the synthesis of dissymmetric (hetero)diarylideneacetones has been developed. Conditions were optimized with a Box-Behnken design of experiment. The milder reaction conditions allow the efficient preparation of fluorinated, or heteroaromatic, dissymmetric diarylideneacetones which cannot be obtained through the classical Claisen-Schmidt protocol. © Georg Thieme Verlag KG · Stuttgart · New York.
Research Center/Unit :
European School of Chemistry, Polymers and Materials, Bioorganic and Medicinal Chemistry, UMR CNRS 7509
Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf
Disciplines :
Chemistry
Author, co-author :
Gendron, Thibault  ;  Université de Liège - ULiège > Département de chimie (sciences) > Chimie organique-nucléaire ; European School of Chemistry, Polymers and Materials, Bioorganic and Medicinal Chemistry, UMR CNRS 7509, 67087 Strasbourg Cedex 2, France ; Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf, 40225 Düsseldorf, Germany
Davioud-Charvet, Elisabeth;  European School of Chemistry, Polymers and Materials, Bioorganic and Medicinal Chemistry, UMR CNRS 7509, 67087 Strasbourg Cedex 2, France
Müller, Thomas J. J.;  Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf, 40225 Düsseldorf, Germany
Language :
English
Title :
Versatile synthesis of dissymmetric diarylideneacetones via a palladium-catalyzed coupling-isomerization reaction
Publication date :
19 November 2012
Journal title :
Synthesis
ISSN :
0039-7881
eISSN :
1437-210X
Publisher :
Georg Thieme Verlag KG
Volume :
44
Issue :
24
Pages :
3829 - 3835
Peer reviewed :
Peer Reviewed verified by ORBi
Funders :
DADD - Deutscher Akademischer Austauschdienst [DE]
Funding text :
This work was supported by the Fonds der Chemischen Industrie, the Deutscher Akademischer Austauschdienst (DAAD, scholarship for T.G.), the collaborative center SFB 544 (B14 project), the Centre National de la Recherche Scientifique (CNRS), the University of Strasbourg (UMR 7509 CNRS-UdS), the ANRémergence program (grant SCHISMAL to E.D.C.), and the International Center for Frontier Research in Chemistry in Strasbourg (www.icfrc.fr). T.G. is grateful to the MENRT (French Ministry of Research) for his PhD salary. We would like to thank Prof. D. Wolbert for his valuable advice on the DoE methodology.
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