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Molecules 2011, 16(8), 6215-6231; doi:10.3390/molecules16086215
Article

The Suzuki Reaction in Aqueous Media Promoted by P, N Ligands

, , ,  and *
Department of Chemistry, University of Nevada, Reno NV 89557, USA
* Author to whom correspondence should be addressed.
Received: 8 June 2011 / Revised: 19 July 2011 / Accepted: 20 July 2011 / Published: 25 July 2011
(This article belongs to the Special Issue Organometallic Chemistry)
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Abstract

The synthesis and structure of palladium complexes of trisubstituted PTA derivatives, PTAR3, are described. Water-soluble phosphine ligands 1,3,5-triaza-7-phosphaadmantane (PTA), tris(aminomethyl)phosphine trihydrobromide, tri(aminomethyl) phosphine, 3,7-dimethyl-1,5,7-triaza-3-phosphabicyclo[3,3,1]nonane (RO-PTA), 3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane (DAPTA), lithium 1,3,5-triaza-7-phosphaadamantane-6-carboxylate (PTA-CO2Li), 2,4,6-triphenyl-1,3,5-triaza-7-phosphatricyclo [3.3.1.1]decane, and 2,4,6-triphenyl-1,3,5-triaza-7-phosphatricyclo[3.3.1.1]decane were used as ligands for palladium catalyzed Suzuki reactions in aqueous media. RO-PTA in combination with palladium acetate or palladium chloride was the most active catalyst for Suzuki cross coupling of aryl bromides and phenylboronic acid at 80 °C in 1:1 water:acetonitrile. The activity of Pd(II) complexes of RO-PTA is comparable to PPh2(m-C6H4SO3Na) (TPPMS) and P(m-C6H4SO3Na)3 (TPPTS) and less active than tri(4,6-dimethyl-3-sulfonatophenyl)phosphine trisodium salt (TXPTS). Activated, deactivated, and sterically hindered aryl bromides were examined, with yields ranging from 50% to 90% in 6 h with 5% palladium precatalyst loading. X-ray crystal structures of (RO-PTA)PdCl2, (PTAR3)2PdCl2 (R = Ph, p-tert-butylC6H5), and PTAR3 (R = p-tert-butylC6H5) are reported.
Keywords: C–C coupling; aqueous phase Suzuki reaction; 1,3,5-triaza-7-phosphaadamantante (PTA); water-soluble phosphine ligands C–C coupling; aqueous phase Suzuki reaction; 1,3,5-triaza-7-phosphaadamantante (PTA); water-soluble phosphine ligands
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Weeden, J.A.; Huang, R.; Galloway, K.D.; Gingrich, P.W.; Frost, B.J. The Suzuki Reaction in Aqueous Media Promoted by P, N Ligands. Molecules 2011, 16, 6215-6231.

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