A supramolecular recyclable catalyst for aqueous Suzuki-Miyaura coupling

Miao Qi, Pei Zi Tan, Fei Xue, Haripal Singh Malhi, Zhong-Xing Zhang, David James Young, Tzi Sum Andy Hor

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    17 Citations (Scopus)

    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 ?-cyclodextrin (?-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)-?-CD (dm?-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

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