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Issue 30, 2015
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Cyclodextrin-based PNN supramolecular assemblies: a new class of pincer-type ligands for aqueous organometallic catalysis

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Abstract

Water-soluble cyclodextrins (CDs) bearing two nitrogen atoms as metal coordinating sites have been synthesized. An appropriate phosphane could be included within their cavity through the primary face to form self-assembled PNN supramolecular edifices. Once the PNN ligands were coordinated to platinum, the resulting complexes proved to be very effective as catalysts in a domino reaction, where a Pt-catalyzed reduction of nitrobenzene was followed by a Paal–Knorr pyrrole reaction. In the nitrobenzene reduction, the modified CDs acted both as first- and second-sphere ligands. Contrary to an acyclic glucopyranose-based NN ligand unable to interact with a phosphane ligand, the CD-based PNN ligands stabilized the catalytic species in water by supramolecular means. Interestingly, the product and the water-soluble Pt-catalyst could be recovered in two different phases once the reaction was complete.

Graphical abstract: Cyclodextrin-based PNN supramolecular assemblies: a new class of pincer-type ligands for aqueous organometallic catalysis

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Publication details

The article was received on 15 May 2015, accepted on 19 Jun 2015 and first published on 19 Jun 2015


Article type: Paper
DOI: 10.1039/C5DT01825K
Author version available: Download Author version (PDF)
Citation: Dalton Trans., 2015,44, 13504-13512
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    Cyclodextrin-based PNN supramolecular assemblies: a new class of pincer-type ligands for aqueous organometallic catalysis

    S. Menuel, E. Bertaut, E. Monflier and F. Hapiot, Dalton Trans., 2015, 44, 13504
    DOI: 10.1039/C5DT01825K

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