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Keywords = 1,3,5-triaza-7-phosphaadmantane (PTA)

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7 pages, 1577 KB  
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7-((5-Bromo-1H-indol-3-yl)(4-methoxyphenyl)methyl)-1,3,5-triaza-7-phosphaadamantan-7-ium Tetrafluoroborate
by Siva Sankar Murthy Bandaru and Carola Schulzke
Molbank 2023, 2023(2), M1636; https://doi.org/10.3390/M1636 - 28 Apr 2023
Viewed by 2525
Abstract
The novel organic salt 7-((5-bromo-1H-indol-3-yl)(4-methoxyphenyl)methyl)1,3,5-triaza-7-phosphaadamantan-7-ium tetrafluoroborate was synthesized from a Lewis acid (LA) and Lewis-base (LB) reaction between 1,3,5-triaza-7-phosphaadmantane (LB) and 5-bromo-3-(4-methoxybenzylidene)-3-H-indol-1-ium tetrafluoroborate (LA). The obtained Lewis acid base adduct, being the title compound, was analyzed and validated by 1H, 13C, [...] Read more.
The novel organic salt 7-((5-bromo-1H-indol-3-yl)(4-methoxyphenyl)methyl)1,3,5-triaza-7-phosphaadamantan-7-ium tetrafluoroborate was synthesized from a Lewis acid (LA) and Lewis-base (LB) reaction between 1,3,5-triaza-7-phosphaadmantane (LB) and 5-bromo-3-(4-methoxybenzylidene)-3-H-indol-1-ium tetrafluoroborate (LA). The obtained Lewis acid base adduct, being the title compound, was analyzed and validated by 1H, 13C, 31P, and 19F 1D-NMR-spectroscopy, ESI mass spectrometry, CHN-elemental analysis, and a single crystal X-ray diffraction investigation. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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17 pages, 620 KB  
Article
The Suzuki Reaction in Aqueous Media Promoted by P, N Ligands
by Jason A. Weeden, Rongcai Huang, Kathryn D. Galloway, Phillip W. Gingrich and Brian J. Frost
Molecules 2011, 16(8), 6215-6231; https://doi.org/10.3390/molecules16086215 - 25 Jul 2011
Cited by 30 | Viewed by 9532
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 [...] Read more.
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. Full article
(This article belongs to the Special Issue Organometallic Chemistry)
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