The Suzuki Reaction in Aqueous Media Promoted by P, N Ligands
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]...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2011-07-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/16/8/6215/ |
| _version_ | 1818138307986456576 |
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| author | Phillip W. Gingrich Brian J. Frost Rongcai Huang Kathryn D. Galloway Jason A. Weeden |
| author_facet | Phillip W. Gingrich Brian J. Frost Rongcai Huang Kathryn D. Galloway Jason A. Weeden |
| author_sort | Phillip W. Gingrich |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-11T10:10:07Z |
| format | Article |
| id | doaj.art-617815aa0f69475d99d7e683043e8e87 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-11T10:10:07Z |
| publishDate | 2011-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-617815aa0f69475d99d7e683043e8e872022-12-22T01:11:47ZengMDPI AGMolecules1420-30492011-07-011686215623110.3390/molecules16086215The Suzuki Reaction in Aqueous Media Promoted by P, N LigandsPhillip W. GingrichBrian J. FrostRongcai HuangKathryn D. GallowayJason A. WeedenThe 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.http://www.mdpi.com/1420-3049/16/8/6215/C–C couplingaqueous phase Suzuki reaction1,3,5-triaza-7-phosphaadamantante (PTA)water-soluble phosphine ligands |
| spellingShingle | Phillip W. Gingrich Brian J. Frost Rongcai Huang Kathryn D. Galloway Jason A. Weeden The Suzuki Reaction in Aqueous Media Promoted by P, N Ligands Molecules C–C coupling aqueous phase Suzuki reaction 1,3,5-triaza-7-phosphaadamantante (PTA) water-soluble phosphine ligands |
| title | The Suzuki Reaction in Aqueous Media Promoted by P, N Ligands |
| title_full | The Suzuki Reaction in Aqueous Media Promoted by P, N Ligands |
| title_fullStr | The Suzuki Reaction in Aqueous Media Promoted by P, N Ligands |
| title_full_unstemmed | The Suzuki Reaction in Aqueous Media Promoted by P, N Ligands |
| title_short | The Suzuki Reaction in Aqueous Media Promoted by P, N Ligands |
| title_sort | suzuki reaction in aqueous media promoted by p n ligands |
| topic | C–C coupling aqueous phase Suzuki reaction 1,3,5-triaza-7-phosphaadamantante (PTA) water-soluble phosphine ligands |
| url | http://www.mdpi.com/1420-3049/16/8/6215/ |
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