Issue 5, 2015

A supramolecular recyclable catalyst for aqueous Suzuki–Miyaura coupling

Abstract

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.

Graphical abstract: A supramolecular recyclable catalyst for aqueous Suzuki–Miyaura coupling

Supplementary files

Article information

Article type
Paper
Submitted
06 Nov 2014
Accepted
02 Dec 2014
First published
02 Dec 2014

RSC Adv., 2015,5, 3590-3596

Author version available

A supramolecular recyclable catalyst for aqueous Suzuki–Miyaura coupling

M. Qi, P. Z. Tan, F. Xue, H. S. Malhi, Z. Zhang, D. J. Young and T. S. A. Hor, RSC Adv., 2015, 5, 3590 DOI: 10.1039/C4RA13953D

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