Aqueous biphasic hydroformylation in the presence of cyclodextrins mixtures: evidence of a positive synergistic effect

Ferreira, Michel; Legrand, François-Xavier; Machut, C.; Bricout, H.; Tilloy, S.; Monflier, Éric

doi:10.1039/c2dt30646h

Cited by 26 publications

(10 citation statements)

References 28 publications

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“…It was also proposed that similar effects could be envisioned in achiral transformations. Several relatedr eports were published in the followingy ears [30][31][32][33][34][35][36][37][38][39][40][41] showing that not only optical purity but also diastereoselectivity,r egioselectivity,a nd reaction rate can be enhanced when ligand mixtures are employed. In the work of Reetza nd Li, [34] the observation of enhanced reaction rates with ligand mixtures was considered as mechanistice vidence for the involvement of mixed MLL'-type species.…”

Section: Resultsmentioning

confidence: 99%

Expansion of the Concept of Nonlinear Effects in Catalytic Reactions Beyond Asymmetric Catalysis

Pollice

Schnürch

2016

Chemistry A European J

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The observation and investigation of nonlinear effects in catalytic reactions provides valuable mechanistic insight. However, the applicability of this method was, until now, limited to molecules possessing chirality and therefore to asymmetric synthesis. The concept of nonlinear effects is expanded to catalytic reactions beyond asymmetric catalysis by using derivatives instead of enantiomers and by considering rates instead of enantiomeric excess. Additionally, its systematic application to investigate the mechanism of catalytic reactions is presented. By exceeding the limitation to asymmetric reactions, the study of nonlinear effects can become a general tool to elucidate reaction mechanisms.

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Section: Resultsmentioning

confidence: 99%

Expansion of the Concept of Nonlinear Effects in Catalytic Reactions Beyond Asymmetric Catalysis

Pollice

Schnürch

2016

Chemistry A European J

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“…However, the same process cannot be applied to longer chain olefins (>C4), their poor solubility in water leading to poor reaction rates. Many strategies have been developed to overcome this issue, among which use of cosolvents [5][6][7] or phase transfer agents such as cyclodextrins [8,9] or activated carbons [10]. On the other hand, surfactants or amphiphilic ligands can also create organic substrate-rich nano-objects (micelles) within the aqueous catalyst phase.…”

Section: Introductionmentioning

confidence: 99%

Aqueous phase homogeneous catalysis using core–shell nanoreactors: Application to rhodium-catalyzed hydroformylation of 1-octene

Cardozo

Julcour-Lebigue

Barthe

et al. 2015

Journal of Catalysis

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High catalytic activity (turnover frequencies up to 700 h À1) was achieved using new triphenylphosphinefunctionalized core cross-linked micelles, TPP@CCM, as nanoreactors and [Rh(acac)(CO) 2 ] as catalyst precursor for the aqueous biphasic hydroformylation of 1-octene. While the hydrophobic core of the polymer offers an adequate environment for the catalytic reaction, its hydrophilic shell confines the catalyst into the aqueous phase and prevents extensive leaching toward the substrate/product phase. Selectivity is better than that of the homogeneous reaction catalyzed by the Rh/PPh 3 system, with minor isomerization and linear to branched aldehyde ratios (l/b) between 3 and 6. Various operating parameters, such as catalyst/ligand concentration, temperature, and P/Rh ratio, were varied and proved that these nanoreactors do not suffer from significant mass transfer limitations. The effect of the nanoreactor hydrophobic core size and degree of functionalization on activity and on l/b regioselectivity has also been investigated. The possible causes of catalyst leaching are discussed.

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“…Interestingly, a synergetic effect between randomly methylated α-and β-CDs has been evidenced in Rh-catalyzed hydroformylation of 1-tetradecene [55]. Indeed, a marked positive nonlinear effect on 1-tetradecene conversion was observed when the CD molar ratio in the mixture was modified.…”

Section: Effect Of Modified Cyclodextrins Upon Catalytic Activitymentioning

confidence: 93%

Hydroformylation in Aqueous Biphasic Media Assisted by Molecular Receptors

Hapiot

Bricout

Tilloy

et al. 2013

Topics in Current Chemistry

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The role of molecular receptors in aqueous biphasic hydroformylation of higher olefins is highlighted through a detailed analysis of their molecular recognition properties. The behavior of cyclodextrins and calixarenes as molecular receptors is especially emphasized and discussed. Their supramolecular interactions with the substrates and the water-soluble ligands proved to be an essential parameter guiding the reaction performances. The hydroformylation activity and chemo- and regio-selectivities can thus be accurately controlled by a suitable match between the receptor and the reaction components. Development outlooks are also presented.

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Aqueous biphasic hydroformylation in the presence of cyclodextrins mixtures: evidence of a positive synergistic effect

Cited by 26 publications

References 28 publications

Expansion of the Concept of Nonlinear Effects in Catalytic Reactions Beyond Asymmetric Catalysis

Expansion of the Concept of Nonlinear Effects in Catalytic Reactions Beyond Asymmetric Catalysis

Aqueous phase homogeneous catalysis using core–shell nanoreactors: Application to rhodium-catalyzed hydroformylation of 1-octene

Hydroformylation in Aqueous Biphasic Media Assisted by Molecular Receptors

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