One-Pot Synthesis of (+)-Nootkatone via ...
Document type :
Article dans une revue scientifique
DOI :
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Title :
One-Pot Synthesis of (+)-Nootkatone via Dark Singlet Oxygenation of Valencene: The Triple Role of the Amphiphilic Molybdate Catalyst
Author(s) :
Hong, Bing [Auteur]
Unité de Catalyse et Chimie du Solide - UMR 8181 [UCCS]
Lebeuf, Raphael [Auteur]
Unité de Catalyse et Chimie du Solide - UMR 8181 [UCCS]
Delbaere, Stephanie [Auteur]
Laboratoire de Spectrochimie et Raman (LASIR) - UMR 8516
Laboratoire Avancé de Spectroscopie pour les Intéractions la Réactivité et l'Environnement - UMR 8516 [LASIRE]
Alsters, Paul [Auteur]
Chemelot Innovation and Learning Labs (Geleen, Pays-Bas)
Rataj, Véronique [Auteur]
Unité de Catalyse et Chimie du Solide - UMR 8181 [UCCS]
Unité de Catalyse et Chimie du Solide - UMR 8181 [UCCS]
Lebeuf, Raphael [Auteur]
Unité de Catalyse et Chimie du Solide - UMR 8181 [UCCS]
Delbaere, Stephanie [Auteur]
Laboratoire de Spectrochimie et Raman (LASIR) - UMR 8516
Laboratoire Avancé de Spectroscopie pour les Intéractions la Réactivité et l'Environnement - UMR 8516 [LASIRE]
Alsters, Paul [Auteur]
Chemelot Innovation and Learning Labs (Geleen, Pays-Bas)
Rataj, Véronique [Auteur]
Unité de Catalyse et Chimie du Solide - UMR 8181 [UCCS]
Journal title :
Catalysts
Volume number :
6
Pages :
184
Publisher :
MDPI
Publication date :
2016-12-26
ISSN :
2073-4344
HAL domain(s) :
Chimie/Chimie organique
English abstract : [en]
Efficient one-pot catalytic synthesis of (+)-nootkatone was performed from (+)-valencene using only hydrogen peroxide and amphiphilic molybdate ions. The process required no solvent and proceeded in three cascade reactions: ...
Show more >Efficient one-pot catalytic synthesis of (+)-nootkatone was performed from (+)-valencene using only hydrogen peroxide and amphiphilic molybdate ions. The process required no solvent and proceeded in three cascade reactions: (i) singlet oxygenation of valencene according to the ene reaction; (ii) Schenck rearrangement of one hydroperoxide into the secondary β-hydroperoxide; and (iii) dehydration of the hydroperoxide into the desired (+)-nootkatone. The solvent effect on the hydroperoxide rearrangement is herein discussed. The amphiphilic dimethyldioctyl ammonium molybdate, which is also a balanced surfactant, played a triple role in this process, as molybdate ions catalyzed at both Step 1 and Step 3 and it allowed the rapid formation of a three-phase microemulsion system that highly facilitates product recovery. Preparative synthesis of the high added value (+)-nootkatone was thus performed at room temperature with an isolated yield of 46.5%. This is also the first example of a conversion of allylic hydroperoxides into ketones catalyzed by molybdate ions.Show less >
Show more >Efficient one-pot catalytic synthesis of (+)-nootkatone was performed from (+)-valencene using only hydrogen peroxide and amphiphilic molybdate ions. The process required no solvent and proceeded in three cascade reactions: (i) singlet oxygenation of valencene according to the ene reaction; (ii) Schenck rearrangement of one hydroperoxide into the secondary β-hydroperoxide; and (iii) dehydration of the hydroperoxide into the desired (+)-nootkatone. The solvent effect on the hydroperoxide rearrangement is herein discussed. The amphiphilic dimethyldioctyl ammonium molybdate, which is also a balanced surfactant, played a triple role in this process, as molybdate ions catalyzed at both Step 1 and Step 3 and it allowed the rapid formation of a three-phase microemulsion system that highly facilitates product recovery. Preparative synthesis of the high added value (+)-nootkatone was thus performed at room temperature with an isolated yield of 46.5%. This is also the first example of a conversion of allylic hydroperoxides into ketones catalyzed by molybdate ions.Show less >
Language :
Anglais
Audience :
Internationale
Popular science :
Non
Administrative institution(s) :
ENSCL
CNRS
Centrale Lille
Univ. Artois
Université de Lille
CNRS
Centrale Lille
Univ. Artois
Université de Lille
Collections :
Research team(s) :
Colloïdes catalyse oxydation (CÏSCO)
Submission date :
2019-09-25T14:37:45Z
2022-11-16T08:26:32Z
2022-11-16T08:26:32Z
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