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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| Format: | Article |
| Language: | English |
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MDPI AG
2018-03-01
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| Series: | Catalysts |
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| Online Access: | http://www.mdpi.com/2073-4344/8/3/115 |
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| author | Geoffrey Dumonteil Marie-Aude Hiebel Sabine Berteina-Raboin |
| author_facet | Geoffrey Dumonteil Marie-Aude Hiebel Sabine Berteina-Raboin |
| author_sort | Geoffrey Dumonteil |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-04-12T05:50:00Z |
| format | Article |
| id | doaj.art-cfd72753b54d4f8baee15dd70b486dea |
| institution | Directory Open Access Journal |
| issn | 2073-4344 |
| language | English |
| last_indexed | 2024-04-12T05:50:00Z |
| publishDate | 2018-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Catalysts |
| spelling | doaj.art-cfd72753b54d4f8baee15dd70b486dea2022-12-22T03:45:20ZengMDPI AGCatalysts2073-43442018-03-018311510.3390/catal8030115catal8030115Solvent-Free Mizoroki-Heck Reaction Applied to the Synthesis of Abscisic Acid and Some DerivativesGeoffrey Dumonteil0Marie-Aude Hiebel1Sabine Berteina-Raboin2Institut de Chimie Organique et Analytique (ICOA), Université d’Orléans UMR CNRS 7311, BP 6759, rue de Chartres, 45067 Orleans CEDEX 2, FranceInstitut de Chimie Organique et Analytique (ICOA), Université d’Orléans UMR CNRS 7311, BP 6759, rue de Chartres, 45067 Orleans CEDEX 2, FranceInstitut de Chimie Organique et Analytique (ICOA), Université d’Orléans UMR CNRS 7311, BP 6759, rue de Chartres, 45067 Orleans CEDEX 2, FranceAbscisic 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.http://www.mdpi.com/2073-4344/8/3/115Mizoroki-Heckabscisic acidsolvent-free |
| spellingShingle | Geoffrey Dumonteil Marie-Aude Hiebel Sabine Berteina-Raboin Solvent-Free Mizoroki-Heck Reaction Applied to the Synthesis of Abscisic Acid and Some Derivatives Catalysts Mizoroki-Heck abscisic acid solvent-free |
| title | Solvent-Free Mizoroki-Heck Reaction Applied to the Synthesis of Abscisic Acid and Some Derivatives |
| title_full | Solvent-Free Mizoroki-Heck Reaction Applied to the Synthesis of Abscisic Acid and Some Derivatives |
| title_fullStr | Solvent-Free Mizoroki-Heck Reaction Applied to the Synthesis of Abscisic Acid and Some Derivatives |
| title_full_unstemmed | Solvent-Free Mizoroki-Heck Reaction Applied to the Synthesis of Abscisic Acid and Some Derivatives |
| title_short | Solvent-Free Mizoroki-Heck Reaction Applied to the Synthesis of Abscisic Acid and Some Derivatives |
| title_sort | solvent free mizoroki heck reaction applied to the synthesis of abscisic acid and some derivatives |
| topic | Mizoroki-Heck abscisic acid solvent-free |
| url | http://www.mdpi.com/2073-4344/8/3/115 |
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