Solvent-Free Mizoroki-Heck Reaction Applied to the Synthesis of Abscisic Acid and Some Derivatives

Abscisic acid (ABA) is a natural product, which is a well-known phytohormone. However, this molecule has recently exhibited interesting biological activities, emphasizing the need for a simple and direct access to new analogues based on the ABA framework. Our strategy relies on a pallado-catalyzed M...

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Bibliographic Details
Published in:Catalysts 2018-03, Vol.8 (3), p.115
Main Authors: Dumonteil, Geoffrey, Hiebel, Marie-Aude, Berteina-Raboin, Sabine
Format: Article
Language:English
Subjects:
Abscisic acid
Catalysts
Chemical reactions
Chemical synthesis
Cross coupling
Dienes
Isomerization
Mizoroki-Heck
solvent-free
Solvents
Trienes
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Summary:Abscisic acid (ABA) is a natural product, which is a well-known phytohormone. However, this molecule has recently exhibited interesting biological activities, emphasizing the need for a simple and direct access to new analogues based on the ABA framework. Our strategy relies on a pallado-catalyzed Mizoroki-Heck cross-coupling as key reaction performed in solvent and ligand free conditions. After a careful optimization, we succeeded in accessing various (E/Z)-dienes and (E/E/Z)-trienes in moderate to good yields without isomerization and applied the same approach to the synthesis of ABA in an environmentally sound manner.
ISSN:2073-4344
2073-4344
DOI:10.3390/catal8030115