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Pd/C as a Reusable Catalyst for the Coupling Reaction of Halophenols and Arylboronic Acids in Aqueous Media

Hidehiro Sakurai, Tatsuya Tsukada and Toshikazu Hirao*

*Department of Applied Chemistry, Faculty of Engineering, Osaka University, Yamada-oka, Suita, Osaka 565-0871, Japan, Email: hiraoap.chem.eng.osaka-u.ac.jp

H. Sakurai, T. Tsukuda, T. Hirao, J. Org. Chem, 2002, 67, 2721-2722.

DOI: 10.1021/jo016342k (free Supporting Information)

Abstract

The Suzuki-Miyaura coupling reaction of halophenols with ArB(OH)2 in aqueous K2CO3 solution is efficiently catalyzed by Pd/C. The palladium catalyst can be reused.

Halophenol
 		 Boronic Acid
 		 Yield (%, isol.)
 
2-Iodophenol PhB(OH)2 70
4-Iodophenol PhB(OH)2

run 1,  2,  3,  4,  5,  6 :
99, 95, 94, 90, 89, 89
4-Iodophenol 2-MeOC6H4B(OH)2 98
4-Bromophenol PhB(OH)2 35 (r.t.), 76 (50°C)

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Key Words

Suzuki Coupling, Biaryls

ID: J42-Y2002-120