Impact of cyclodextrins on the behavior of amphiphilic ligands in aqueous organometallic catalysis

Impact of cyclodextrins on the behavior of amphiphilic ligands in aqueous organometallic catalysis

In this study, we showed that the addition of randomly modified β-cyclodextrin (RAME-β-CD) in aqueous medium could have a beneficial impact on the catalytic performances of phosphane-based aggregates in the Pd-catalyzed cleavage of allyl carbonates (Tsuji–Trost reaction). The RAME-β-CD/phosphane sup...

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Main Authors: Hervé Bricout, Estelle Léonard, Christophe Len, David Landy, Frédéric Hapiot, Eric Monflier
Format: Article
Language:English
Published: Beilstein-Institut 2012-09-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
amphiphilic phosphanes
biphasic system
cyclodextrins
micelles
Online Access:https://doi.org/10.3762/bjoc.8.167
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spelling doaj-70a5749019e542dea9d8be6fd9408e5b2021-03-02T11:05:06ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972012-09-01811479148410.3762/bjoc.8.1671860-5397-8-167Impact of cyclodextrins on the behavior of amphiphilic ligands in aqueous organometallic catalysisHervé Bricout0Estelle Léonard1Christophe Len2David Landy3Frédéric Hapiot4Eric Monflier5Université Lille Nord de France, CNRS UMR 8181, Unité de Catalyse et de Chimie du Solide - UCCS, UArtois, Faculté des Sciences Jean Perrin, SP18, 62307 Lens Cedex, FranceUniversité de Technologie de Compiègne, Transformation Intégrée de la Matière Renouvelable, EA 4297 UTC/ESCOM Centre de recherches de Royallieu, BP 20529, F-60205 Compiègne Cedex, FranceUniversité de Technologie de Compiègne, Transformation Intégrée de la Matière Renouvelable, EA 4297 UTC/ESCOM Centre de recherches de Royallieu, BP 20529, F-60205 Compiègne Cedex, FranceUniversité Lille Nord de France, UCEIV, ULCO, 145, Avenue Maurice Schumann, MREI 1, F-59140 Dunkerque, FranceUniversité Lille Nord de France, CNRS UMR 8181, Unité de Catalyse et de Chimie du Solide - UCCS, UArtois, Faculté des Sciences Jean Perrin, SP18, 62307 Lens Cedex, FranceUniversité Lille Nord de France, CNRS UMR 8181, Unité de Catalyse et de Chimie du Solide - UCCS, UArtois, Faculté des Sciences Jean Perrin, SP18, 62307 Lens Cedex, FranceIn this study, we showed that the addition of randomly modified β-cyclodextrin (RAME-β-CD) in aqueous medium could have a beneficial impact on the catalytic performances of phosphane-based aggregates in the Pd-catalyzed cleavage of allyl carbonates (Tsuji–Trost reaction). The RAME-β-CD/phosphane supramolecular interactions helped explain the catalytic results. The presence of RAME-β-CD in the aqueous compartment improved the phosphane-based aggregate dynamics. The exchanges between the hydrophobic substrate-containing aggregate core and the catalyst-containing aqueous phase were then greatly favored, resulting in an increase in the catalytic performances.https://doi.org/10.3762/bjoc.8.167amphiphilic phosphanesbiphasic systemcyclodextrinsmicelles
collection DOAJ
language English
format Article
sources DOAJ
author Hervé Bricout
Estelle Léonard
Christophe Len
David Landy
Frédéric Hapiot
Eric Monflier
spellingShingle Hervé Bricout
Estelle Léonard
Christophe Len
David Landy
Frédéric Hapiot
Eric Monflier
Impact of cyclodextrins on the behavior of amphiphilic ligands in aqueous organometallic catalysis
Beilstein Journal of Organic Chemistry
amphiphilic phosphanes
biphasic system
cyclodextrins
micelles
author_facet Hervé Bricout
Estelle Léonard
Christophe Len
David Landy
Frédéric Hapiot
Eric Monflier
author_sort Hervé Bricout
title Impact of cyclodextrins on the behavior of amphiphilic ligands in aqueous organometallic catalysis
title_short Impact of cyclodextrins on the behavior of amphiphilic ligands in aqueous organometallic catalysis
title_full Impact of cyclodextrins on the behavior of amphiphilic ligands in aqueous organometallic catalysis
title_fullStr Impact of cyclodextrins on the behavior of amphiphilic ligands in aqueous organometallic catalysis
title_full_unstemmed Impact of cyclodextrins on the behavior of amphiphilic ligands in aqueous organometallic catalysis
title_sort impact of cyclodextrins on the behavior of amphiphilic ligands in aqueous organometallic catalysis
publisher Beilstein-Institut
series Beilstein Journal of Organic Chemistry
issn 1860-5397
publishDate 2012-09-01
description In this study, we showed that the addition of randomly modified β-cyclodextrin (RAME-β-CD) in aqueous medium could have a beneficial impact on the catalytic performances of phosphane-based aggregates in the Pd-catalyzed cleavage of allyl carbonates (Tsuji–Trost reaction). The RAME-β-CD/phosphane supramolecular interactions helped explain the catalytic results. The presence of RAME-β-CD in the aqueous compartment improved the phosphane-based aggregate dynamics. The exchanges between the hydrophobic substrate-containing aggregate core and the catalyst-containing aqueous phase were then greatly favored, resulting in an increase in the catalytic performances.
topic amphiphilic phosphanes
biphasic system
cyclodextrins
micelles
url https://doi.org/10.3762/bjoc.8.167
work_keys_str_mv AT hervebricout impactofcyclodextrinsonthebehaviorofamphiphilicligandsinaqueousorganometalliccatalysis
AT estelleleonard impactofcyclodextrinsonthebehaviorofamphiphilicligandsinaqueousorganometalliccatalysis
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AT davidlandy impactofcyclodextrinsonthebehaviorofamphiphilicligandsinaqueousorganometalliccatalysis
AT frederichapiot impactofcyclodextrinsonthebehaviorofamphiphilicligandsinaqueousorganometalliccatalysis
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