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Issue 17, 2017
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Water-soluble phosphane-substituted cyclodextrin as an effective bifunctional additive in hydroformylation of higher olefins

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Abstract

In cyclodextrin (CD)-mediated aqueous biphasic catalysis, favoring contacts between the CD (“host”), the organic substrate (“guest”) and the water-soluble catalyst is crucial for the reaction to proceed efficiently at the aqueous/organic interface. Grafting the catalyst onto the CD backbone thus appears as an attractive approach to favor the molecular recognition of the substrate and its subsequent catalytic conversion into products. In this context, a new water-soluble β-CD-based phosphane was synthesized and characterized by NMR, tensiometric and ITC measurements. The β-CD-based phosphane consisted of a 3,3′-disulfonatodiphenyl phosphane connected to the primary face of β-CD by a dimethyleneamino spacer. Intra- and intermolecular inclusion processes of one of the two sulfophenyl groups into the β-CD cavity were identified in water. However, the association constant (Ka) related to the β-CD/sulfophenyl group couple was low. Accordingly, the inclusion process was easily displaced upon coordination to rhodium complexes. The efficacy of the resulting Rh-complex coordinated by β-CD-based phosphanes was assessed in Rh-catalyzed hydroformylation of higher olefins. The catalytic system proved to be far more successful and efficient than a system consisting of supramolecularly interacting phosphanes and CDs. The catalytic activity was up to 30-fold higher while the chemo- and regioselectivities remain rather unchanged.

Graphical abstract: Water-soluble phosphane-substituted cyclodextrin as an effective bifunctional additive in hydroformylation of higher olefins

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Publication details

The article was received on 02 Jun 2017, accepted on 19 Jul 2017 and first published on 24 Jul 2017


Article type: Paper
DOI: 10.1039/C7CY01108C
Citation: Catal. Sci. Technol., 2017,7, 3823-3830
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    Water-soluble phosphane-substituted cyclodextrin as an effective bifunctional additive in hydroformylation of higher olefins

    J. Leblond, J. Potier, S. Menuel, H. Bricout, C. Machut-Binkowski, D. Landy, S. Tilloy, E. Monflier and F. Hapiot, Catal. Sci. Technol., 2017, 7, 3823
    DOI: 10.1039/C7CY01108C

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