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Synfacts 2007(10): 1112-1112  
DOI: 10.1055/s-2007-968967
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Aqueous Suzuki-Miyaura Coupling with Pd/C

Contributor(s): Yasuhiro Uozumi, Hiroe Takenaka
T. Maegawa, Y. Kitamura, S. Sako, T. Udzu, A. Sakurai, A. Tanaka, Y. Kobayashi, K. Endo, U. Bora, T. Kurita, A. Kozaki, Y. Monguchi, H. Sajiki*
Gifu Pharmaceutical University, Japan
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Publication History

Publication Date:
07 November 2007 (online)

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Significance

Palladium-catalyzed cross-coupling reactions of aryl halides (or pseudohalides) and aryl (or vinyl) boronic acids, the so-called Suzuki-Miyaura coupling, were examined under aqueous conditions with a palladium/charcoal catalyst. The conditions depicted in the scheme were identified as the best conditions among 15 solvents, nine base-solvent combinations, and seven different Pd/C. Remarkably wide substrate tolerance was achieved under the optimized conditions. Little palladium leaching was observed (less than the detection limit of ICP-Mass analysis) from the reaction mixture.