Efficient Suzuki cross-coupling reaction using aryl bromides in water

ORGN 199

Zhiqiang Zhang1, Jingbo Yan2, Zhizhi Hu2, Ben Li2, Ren He3, Peng Lei2, and Haijun Chi2. (1) 1. Key Laboratory of Fine Chemical Engineering; 2. School of Chemical Engineering, 1. Dalian University of Technology; 2. Anshan University of Science & Technology, Anshan, 114044, China, (2) School of Chemical Engineering, Anshan University of Science & Technology, Anshan, 114044, China, (3) Key Laboratory of Fine Chemical Engineering, Dalian University of Technology, Dalian, 116012, China
Palladium-catalyzed cross-coupling reactions utilizing aryl halides has become a widely used strategy for the formation of new carbon-carbon bonds and in particular for the synthesis of biaryls. The replacement of expensive, toxic, and flammable organic solvents by water is highly desirable for reducing costs and for developing environmentally benign synthetic reactions that facilitate catalyst recycling. Herein, we report an efficient Suzuki cross-coupling reaction using a variety of aryl bromides in neat water. Employing air- and moisture-stable palladium-phosphinous acid catalyst [(t-Bu)2P(OH)]2PdCl2 (POPd) allows formation of biaryls from aryl bromides in good to high yields. Functional groups such as ketones, methoxyls, formyl and nitriles are tolerated, and organic cosolvents are not required. The feasibility of catalyst recyling has also been demonstrated.
 

Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Combinatorial, Parallel, and Solid-Phase Chemistry
8:00 PM-10:00 PM, Sunday, 10 September 2006 Moscone Center -- Hall D, Poster

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006