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Synfacts 2009(6): 0687-0687
DOI: 10.1055/s-0029-1216762
DOI: 10.1055/s-0029-1216762
Polymer-Supported Synthesis
© Georg Thieme Verlag
Stuttgart ˙ New York
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
Further Information
Publication History
Publication Date:
25 May 2009 (online)
![](https://www.thieme-connect.de/media/synfacts/200906/lookinside/thumbnails/10.1055-s-0029-1216762-1.jpg)
Significance
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.