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Synthesis 2012; 44(24): 3829-3835
DOI: 10.1055/s-0032-1316811
DOI: 10.1055/s-0032-1316811
paper
Versatile Synthesis of Dissymmetric Diarylideneacetones via a Palladium-Catalyzed Coupling–Isomerization Reaction
Further Information
Publication History
Received: 21 September 2012
Accepted after revision: 24 October 2012
Publication Date:
15 November 2012 (online)
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 effectsSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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