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Molecules 2012, 17(11), 13062-13072; doi:10.3390/molecules171113062

Phosphane-Based Cyclodextrins as Mass Transfer Agents and Ligands for Aqueous Organometallic Catalysis

Unité de Catalyse et de Chimie du Solide (UCCS), CNRS, UMR 8181, Univ. Artois, Rue Jean Souvraz, SP 18, F-62307 Lens, France
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Received: 11 October 2012 / Revised: 30 October 2012 / Accepted: 30 October 2012 / Published: 2 November 2012
(This article belongs to the Special Issue Phase Transfer Catalysis)
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Abstract

The replacement of hazardous solvents and the utilization of catalytic processes are two key points of the green chemistry movement, so aqueous organometallic catalytic processes are of great interest in this context. Nevertheless, these processes require not only the use of water-soluble ligands such as phosphanes to solubilise the transition metals in water, but also the use of mass transfer agents to increase the solubility of organic substrates in water. In this context, phosphanes based on a cyclodextrin skeleton are an interesting alternative since these compounds can simultaneously act as mass transfer agents and as coordinating species towards transition metals. For twenty years, various cyclodextrin-functionalized phosphanes have been described in the literature. Nevertheless, while their coordinating properties towards transition metals and their catalytic properties were fully detailed, their mass transfer agent properties were much less discussed. As these mass transfer agent properties are directly linked to the availability of the cyclodextrin cavity, the aim of this review is to demonstrate that the nature of the reaction solvent and the nature of the linker between cyclodextrin and phosphorous moieties can deeply influence the recognition properties. In addition, the impact on the catalytic activity will be also discussed.
Keywords: cyclodextrin; hydroformylation; hydrogenation; inclusion; phosphanes; self-inclusion; water-soluble cyclodextrin; hydroformylation; hydrogenation; inclusion; phosphanes; self-inclusion; water-soluble
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Tilloy, S.; Binkowski-Machut, C.; Menuel, S.; Bricout, H.; Monflier, E. Phosphane-Based Cyclodextrins as Mass Transfer Agents and Ligands for Aqueous Organometallic Catalysis. Molecules 2012, 17, 13062-13072.

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