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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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