Versatile Synthesis of Dissymmetric Diarylideneacetones via a Palladium-Catalyzed­ Coupling–Isomerization Reaction

Thibault Gendron; Elisabeth Davioud-Charvet; Thomas J. J. Müller

doi:10.1055/s-0032-1316811

Synthesis, Table of Contents

Synthesis 2012; 44(24): 3829-3835
DOI: 10.1055/s-0032-1316811

paper

Versatile Synthesis of Dissymmetric Diarylideneacetones via a Palladium-Catalyzed Coupling–Isomerization Reaction

Thibault Gendron

^aEuropean School of Chemistry, Polymers and Materials, Bioorganic and Medicinal Chemistry, UMR CNRS 7509, 25 rue Becquerel, 67087 Strasbourg Cedex 2, France

^bInstitut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstr. 1, 40225 Düsseldorf, Germany Fax: +49(211)8114324 Email: thomasjj.mueller@uni-duesseldorf.de

,

Elisabeth Davioud-Charvet

^aEuropean School of Chemistry, Polymers and Materials, Bioorganic and Medicinal Chemistry, UMR CNRS 7509, 25 rue Becquerel, 67087 Strasbourg Cedex 2, France

,

Thomas J. J. Müller*

^bInstitut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstr. 1, 40225 Düsseldorf, Germany Fax: +49(211)8114324 Email: thomasjj.mueller@uni-duesseldorf.de

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Abstract

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Abstract

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.

Key words

heterocycles - catalysis - cross-coupling - isomerization - palladium - solvent effects - substituent effects

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References

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Supporting Information

Versatile Synthesis of Dissymmetric Diarylideneacetones via a Palladium-Catalyzed­ Coupling–Isomerization Reaction

Versatile Synthesis of Dissymmetric Diarylideneacetones via a Palladium-Catalyzed Coupling–Isomerization Reaction