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Synfacts 2005(2): 0262-0262  
DOI: 10.1055/s-2005-916099
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Heterogeneous Suzuki-Miyaura Coupling Catalyzed by a NHC-Pd Complex

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Takayasu Arakawa
J. H. Kim, J. W. Kim, M. Shokouhimehr, Y. S. Lee*
Seoul National University, Korea
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Publication History

Publication Date:
25 October 2005 (online)

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Significance

Poly(1-methylimidazoliummethyl styrene)-surface grafted polystyrene resin 2 was prepared for the first time by suspension polymerization of 1-methyl-3-(4-vinylbenzyl)imidazolium hexafluorophosphate 1, styrene, and DVB in water. A mixture of the resin 2 and Pd(OAc)2 was shaken in DMSO to afford a stable N-heterocyclic carbene (NHC)-Pd complex 3, which was applied to the heterogeneous Suzuki-Miyaura cross-coupling in aqueous DMF at 50 °C for 1-6 h (21 examples). The catalyst 3 was reused ten times in the reaction of iodobenzene with phenylboronic acid without any loss of its catalytic activity.