Tuesday, 27 June 2006
Ponderosa (poster/exhibit) (John Ascuaga’s Nugget Casino Resort)
161

Palladium-Catalyzed Suzuki Coupling Reactions in Aqueous Media Using Water-Soluble Phosphines

Rongcai Huang, Phillip W. Gingrich, and Brian J. Frost. University of Nevada, Reno, NV

Organic catalysis in water is one of the important goals in green chemistry. Water soluble phosphine ligands 1,3,5-triaza-7-phosphaadmantane 1(PTA), tris(aminomethyl)phosphine trihydrobromide 2 and 3,7-dimethyl-1,5,7-triaza-3-phosphabicyclo[3,3,1]nonane 3 were applied to palladium catalyzed Suzuki reactions. Ligand 3, in combination with palladium acetate or palladium chloride gave highly active catalysts for Suzuki cross coupling of aryl bromides with phenylboronic acid at 80oC in 1:1 water:acetonitrile over six hours. Activated, deactivated and sterically hindered aryl bromides gave good results. The yields ranged from 50-90 % at 80oC with 5 % palladium acetate.

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