Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 70, Issue 17, Pages 6714-6720Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo050721m
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[GRAPHICS] Poly(1-methylimidazoliummethyl styrene)-surface grafted-polystyrene) resin was prepared for the first time as a polymer-supported N-heterocyclic carbene (NHC) precursor for palladium complex by suspension polymerization. To prepare this polymer-supported NHC precursor, 1-methyl-3-(4vinylbenzyl)imidazolium hexafluorophosphate, [MVBIM] [PF6-], was synthesized as a monomer and copolymerized with styrene and DVB in water. This polymer-supported NHC precursor with imidazolium as a ligand, which exists solely on the surface of the resin, was well characterized by FE-SEM, CLSM, and IR spectroscopy. The precursor containing imidazolium readily formed a stable complex with Pd(OAc)(2) , and this polymer-supported N-heterocyclic carbene-palladium complex exhibited excellent catalytic activity for Suzuki cross-coupling reaction in an aqueous medium. The catalyst was recovered quantitatively from the reaction mixture by simple filtration and was able to be reused for a number of recycles with consistent activity in all of the coupling reactions.
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