Sodium 2-(2-pyridin-3-ylethylamino)ethyl sulfonate: an efficient ligand and base for palladium-catalyzed Suzuki reaction in aqueous media

Pawar, Shivaji S.; Uppalla, L. S.; Shingare, Murlidhar S.; Thore, Shivaji N.

doi:10.1016/j.tetlet.2008.07.101

Cited by 33 publications

(7 citation statements)

References 57 publications

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“…The catalytic activity of RO-PTA/Pd(OAc) 2 is comparable to Suzuki coupling utilizing water soluble phosphines such as TPPMS and TPPTS [ 19 , 20 , 21 ]. When compared to water soluble TXPTS and palladacylces developed by Shaughnessy et al [ 22 , 23 , 27 ] or water soluble diamine ligands [ 25 , 26 ] catalysis by RO-PTA was much less effective.…”

Section: Resultsmentioning

confidence: 99%

“…Heck [ 2 , 3 ], Suzuki [ 2 , 4 ], Stille [ 5 , 6 ], Sonogashira [ 7 , 8 ], and Buchwald-Hartwig [ 9 , 10 ] couplings are widely used to synthesize natural products, materials, and polymers. Since Casalnuovo’s initial report of palladium-catalyzed cross-coupling reactions in aqueous solvents using TPPMS/Pd(OAc) 2 [ 11 ], a variety of catalytic systems in aqueous media have been developed and used for cross-coupling reactions [ 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 ]. Some recent examples of aqueous phase Suzuki reactions involve sterically demanding ligands [ 12 , 22 , 23 ], ligand free palladium catalysts [ 14 , 24 ], palladium nanoparticles on ionic liquids co-polymerized with styrene [ 15 ], and ZrO 2 impregnated with palladium nanoparticles [ 17 ].…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2011

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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.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

et al. 2011

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“…The catalyst was more effective for coupling reactions run in PEG alone, however. Alkylsulfonate-functionalized pyridine ligand L190 was used as a promoter for the room temperature Heck and Suzuki coupling of aryl iodides in water. , Good yields were obtained, but high palladium loadings (3−5 mol %) were required along with very high loadings of L190 (50−100 mol %).…”

Section: Catalytic Applications Of Hydrophilic Ligandsmentioning

confidence: 99%

Hydrophilic Ligands and Their Application in Aqueous-Phase Metal-Catalyzed Reactions

2009

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“…Also, it is eco-friendly, nontoxic, and non-flammable solvent. 54,55 Herein, we report a new heterogeneous and reusable catalyst for Suzuki-Miyaura cross-coupling reaction in water. The catalyst is not sensitive to air and displays high efficiency for biaryl synthesis.…”

Section: Introductionmentioning

confidence: 99%

Silica-acac-supported palladium nanoparticles as an efficient and reusable heterogeneous catalyst in the Suzuki–Miyaura cross-coupling reaction in water

2014

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Supported Pd nanoparticles on acetyl acetone modified silica gel was prepared and its catalytic application in the Suzuki-Miyaura reaction of various aryl halides with phenylboronic acid was investigated. The reaction was carried out in water as solvent under green conditions in the presence of NaHCO 3 as the base. The catalyst was characterized by a combination of powder XRD, XPS, TEM and SEM. The catalyst is not sensitive to air and moisture, so reactions were carried out without using inert atmosphere. The catalyst can be reused up to six times without significant loss of catalyst activity. The cumulative turnover number (TON) over six runs is 13525.

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Sodium 2-(2-pyridin-3-ylethylamino)ethyl sulfonate: an efficient ligand and base for palladium-catalyzed Suzuki reaction in aqueous media

Cited by 33 publications

References 57 publications

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

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

Hydrophilic Ligands and Their Application in Aqueous-Phase Metal-Catalyzed Reactions

Silica-acac-supported palladium nanoparticles as an efficient and reusable heterogeneous catalyst in the Suzuki–Miyaura cross-coupling reaction in water

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