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Asymmetric Suzuki-Miyaura Coupling in Water Using a Chiral Polymeric Pd Catalyst
Y. Uozumi*, Y. Matsuura, T. Arakawa, Y. M. A. Yamada
Institute for Molecular Science, Aichi and RIKEN, Saitama, Japan
25 May 2009 (online)
Asymmetric Suzuki-Miyaura coupling in water with a novel recyclable palladium complex of a polymer-supported chiral imidazoindole phosphine ligand was described. Thus, PS-PEG-supported imidazoindole dicyclohexylphosphine (PS-PEG-L*, 7) was prepared from PS-PEG-NH2 and compound 6. The reaction of 2-methyl-1-iodonaphthalene with 2-methylnaphthyl boronic acid was catalyzed by the amphiphilic polymeric PS-PEG-L*-Pd complex to give 2,2′-dimethyl-1,1′-binaphthyl in 95% yield with 94% ee (S). The catalyst PS-PEG-L*-Pd was recovered readily and reused four times with little loss of its catalytic activity and stereoselectivity.