A supramolecular recyclable catalyst for aqueous Suzuki-Miyaura coupling

M Qi; P Z Tan; F Xue; H S Malhi; Z X Zhang; David James Young; T S A Hor

doi:10.1039/c4ra13953d

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A supramolecular recyclable catalyst for aqueous Suzuki-Miyaura coupling

Journal article

Peer reviewed

A supramolecular recyclable catalyst for aqueous Suzuki-Miyaura coupling

M Qi, P Z Tan, F Xue, H S Malhi, Z X Zhang, David James Young and T S A Hor

RSC Advances, Vol.5(5), pp.3590-3596

2015

DOI: https://doi.org/10.1039/c4ra13953d

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Abstract

catalyst activity

chemical bonds

crystal structure

hydrophilicity

metal complexes

nuclear magnetic resonance spectroscopy

palladium

single crystals

supramolecular chemistry

synthesis (chemical)

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.

Details

Title: A supramolecular recyclable catalyst for aqueous Suzuki-Miyaura coupling
Authors: M Qi (Author) - Institute of Materials Research and Engineering, Singapore
P Z Tan (Author) - Institute of Materials Research and Engineering, Singapore
F Xue (Author) - Institute of Materials Research and Engineering, Singapore
H S Malhi (Author) - Institute of Materials Research and Engineering, Singapore
Z X Zhang (Author) - Institute of Materials Research and Engineering, Singapore
David James Young (Author) - Monash University, Malaysia
T S A Hor (Author) - Institute of Materials Research and Engineering, Singapore
Publication details: RSC Advances, Vol.5(5), pp.3590-3596
Publisher: Royal Society of Chemistry (R S C) Publications
Date published: 2015
DOI: 10.1039/c4ra13953d
ISSN: 2046-2069; 2046-2069
Organisation Unit: University of the Sunshine Coast, Queensland
Language: English
Record Identifier: 99449133502621
Output Type: Journal article

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Collaboration types: Domestic collaboration; International collaboration
Web Of Science research areas: Chemistry, Multidisciplinary