A supramolecular recyclable catalyst for aqueous Suzuki-Miyaura coupling

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A supramolecular recyclable catalyst for aqueous Suzuki-Miyaura coupling

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Title: A supramolecular recyclable catalyst for aqueous Suzuki-Miyaura coupling
Author/Creator: Qi, M | Tan, P Z | Xue, F | Malhi, H S | Zhang, Z X | Young, David James | Hor, T S A
Description: A water-soluble, supramolecular catalytic system has been designed based on inclusion complexation between a hydrophobic palladium(ii)-dipyrazole complex bearing an adamantyl (Ad) molecular recognition moiety and a complementary, hydrophilic β-cyclodextrin (β-CD) derivative. The single-crystal molecular structure of the Pd(ii) complex was determined and its host-guest inclusion complexation with heptakis(2,6-di-O-methyl)-β-CD (dmβ-CD) in an aqueous medium was confirmed by 2D NOESY 1H NMR spectroscopy. The catalyst showed high activity for Suzuki-Miyaura coupling of hydrophilic aryl bromides with aryl boronic acids in aqueous organic solvents. In the presence of n-Bu4NBr as a stabilizer, the catalyst-containing reaction solution can be recycled and reused multiple times to catalyze the coupling reaction of fresh substrates once the product has been removed by centrifugation. This work demonstrates a supramolecular complex approach, non-covalently modifying a water insoluble metal complex to provide a water-soluble inclusion system to serve as a recyclable catalyst for potential application in green chemical synthesis. This journal is © The Royal Society of Chemistry 2015.
Relation: RSC Advances / Vol. 5, No. 5, pp.3590-3596
Relation: http://dx.doi.org/10.1039/c4ra13953d
Year: 2015
Publisher: Royal Society of Chemistry (R S C) Publications
Subject: FoR 03 (Chemical Sciences) | catalyst activity | chemical bonds | crystal structure | hydrophilicity | metal complexes | nuclear magnetic resonance spectroscopy | palladium | single crystals | supramolecular chemistry | synthesis (chemical)

Resource Type: Journal Article
Identifier: ISSN: 2046-2069
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