Next Article in Journal
Antiradical, Chelating and Antioxidant Activities of Hydroxamic Acids and Hydroxyureas
Previous Article in Journal
New 3′,8′′-Linked Biflavonoids from Selaginella uncinata Displaying Protective Effect against Anoxia
Previous Article in Special Issue
Bent Dinuclear Platinum(II) Halo-Bridged Carbonyl Complexes
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)
Download PDF [620 KB, uploaded 18 June 2014]

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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote
MDPI and ACS Style

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.

View more citation formats

Related Articles

Article Metrics

For more information on the journal, click here

Comments

Cited By

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert