A supramolecular recyclable catalyst for aqueous Suzuki-Miyaura coupling

Miao Qi, Pei Zi Tan, Fei Xue, Haripal Singh Malhi, Zhong Xing Zhang, David J. Young, T. S.Andy Hor

Research output: Contribution to journalArticle

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. 

Original languageEnglish
Pages (from-to)3590-3596
Number of pages7
JournalRSC Advances
Volume5
Issue number5
DOIs
Publication statusPublished - 2015
Externally publishedYes

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    Qi, M., Tan, P. Z., Xue, F., Malhi, H. S., Zhang, Z. X., Young, D. J., & Hor, T. S. A. (2015). A supramolecular recyclable catalyst for aqueous Suzuki-Miyaura coupling. RSC Advances, 5(5), 3590-3596. https://doi.org/10.1039/c4ra13953d