A supramolecular recyclable catalyst for aqueous Suzuki-Miyaura couplingElectronic supplementary information (ESI) available: General measurement and experimental methods; a table of single crystal data and structure refinement parameters for adamantyl-containing Pd(ii) complex (Ad-L-PdCl2); 1H NMR spectra of Ad-L and Ad-L-PdCl2; calibration curve based on 1H NMR analysis for the yield calculation for Suzuki-Miyaura coupling reaction. CCDC 1031688. For ESI and crystallographic data in CIF or oth

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 1 H 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 -Bu 4 NBr 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. A Pd( ii ) pyrazolyl complex is solubilized by host-guest inclusion to give an efficient, recyclable catalyst for Suzuki-Miyaura couplings in aqueous-organic solvents.