Palladium(<scp>ii</scp>) complexes bearing the 1,2,3-triazole based organosulfur/ selenium ligand: synthesis, structure and applications in Heck and Suzuki–Miyaura coupling as a catalyst via palladium nanoparticles

Saleem, Fariha; Rao, Gyandshwar Kumar; Kumar, Arun; Kumar, Satyendra; Singh, Mahabir P.; Singh, Ajai K.

doi:10.1039/c4ra09574j

Cited by 56 publications

(127 citation statements)

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“…Organochalcogen ligands, such as sulfur ylides, show rivalry with their respective phosphorus ylide analogues for releasing of Pd(0) species in the Suzuki-Miyaura reaction [26]. The low catalyst loading and more environmentally safe reagent than the other organometallic reagents make these ligands and their Pd(II) complexes ideal catalysts for the Suzuki-Miyaura reaction [27,28].…”

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A new Pd(II) complex of a sulfur ylide; Synthesis, X-ray characterization, theoretical study and catalytic activity toward the Suzuki–Miyaura reaction

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A new Pd(II) complex of a sulfur ylide; Synthesis, X-ray characterization, theoretical study and catalytic activity toward the Suzuki–Miyaura reaction

et al. 2016

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“…Palladium (II) complexes have been extensively used as catalysts 18,19 in homogeneous phase in reactions such as the CO 2 hydrogenation to obtain methanol, 20 the preparation of biodiesel, 21 the cross coupling reactions in organic synthesis 22 , 23 and the hydrogenation of alkenes. [24][25][26][27][28][29][30][31] These last reactions are widely used in processes such as in the hydrogenation of petroleum cracking byproducts and in the fatty acid hydrogenation.…”

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confidence: 99%

New hybrid materials based on the grafting of Pd(ii)-amino complexes on the graphitic surface of AC: preparation, structures and catalytic properties

et al. 2016

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2 S-F/Pd(II) hybrids on the hydrogenation of 1-octene in methanol as a catalytic test were evaluated. 100 % conversion to n-octane at T = 323.1 K and P = 15 bar, was obtained with both catalysts and most of Pd(II) was reduced to Pd(0) nanoparticles, which remained on the AC surface. Reusing of the catalysts in three additional cycles reveals that the catalyst bearing the F ligand with larger Pd-complexing ability showed no loss of activity (100 % conversion to n-octane) which is assigned to its larger structural stability. The catalyst with the weaker F ligand underwent progressive loss of activity (from 100 % to 79 % in four cycles), due to the constant aggregation of the Pd (0) nanoparticles. Milder conditions, T = 303.1 K and P =1.5 bar, prevent the aggregation of the Pd(0) nanoparticles in this catalyst allowing the retaining of high catalytic efficiency (100 % conversion) in four reaction cycles.

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“…In TGA plots of all complexes (see Figs. 52(11); N(3)─Pd(1)─Cl(2) 93.6(2); Cl(1)─Pd(1)─Cl (2) (12) and 2.2815 (12) Å] are normal. NMR spectra.…”

Section: Resultsmentioning

confidence: 99%

“…mild reaction conditions, excellent functional group tolerance, selectivity and simple work up procedure which results in quantitative yield, give 'Click' reaction an edge over other protocols. 5,[9][10][11][12] The ligand architecture is considered important to design an efficient catalyst. Thus functionalized 1,2,3-triazoles constitute a class of versatile ligands for a variety of metal ions.…”

Section: Introductionmentioning

confidence: 99%

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‘Click’ generated 1,2,3-triazole based organosulfur/selenium ligands and their Pd(ii) and Ru(ii) complexes: their synthesis, structure and catalytic applications

2016

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1-(2,6-Diisopropylphenyl)-4-(phenylthio/selenomethyl)-1H-1,2,3-triazole (L1/L2) was synthesized by a 'Click' reaction and treated with [Pd(CH3CN)2Cl2] for 5 h or [(η(6)-C6H6)RuCl(μ-Cl)]2 for 8 h (followed by reaction with NH4PF6) at room temperature, resulting in complexes [Pd(L)Cl2] (1 and 2) or [(η(6)-C6H6)Ru(L)Cl]PF6 (3 and 4) (L = L1 or L2), respectively. The four complexes (1-4) and ligands (L1 and L2) were characterized with (1)H, (13)C{(1)H} and (77)Se{(1)H} NMR spectroscopy and high resolution mass spectrometry. The single crystal structures of 1-4 were solved. The geometry of Pd in 1 and 2 is distorted square planar. The Pd-S and Pd-Se bond distances in 1 and 2 are 2.277(3) and 2.384(6) Å respectively. In 3 and 4, there is a pseudo-octahedral "piano-stool" type disposition of donor atoms around Ru. The Ru-S and Ru-Se bond lengths in 3 and 4 are 2.3728(12) and 2.4741(6) Å respectively. The catalytic activity of complexes 1 and 2 was explored for Suzuki-Miyaura coupling (SMC) in water and the Sonogashira coupling reaction. For various aryl bromides, including deactivated ones, complexes 1 and 2 were found to be efficient catalysts for both couplings. The optimum loading of 1 and 2 required to catalyze both coupling reactions is of the order of 0.001-2 mol% of Pd. For SMC, no additive or phase transfer catalyst was added. For catalysis of the transfer hydrogenation (TH) of aldehydes and ketones, the half-sandwich Ru(ii) complexes 3 and 4 were explored. Their optimum catalytic loading was found to be 0.1-0.4 mol% of Ru. For TH, both the water solvent and the glycerol hydrogen source are environmentally friendly. The catalytic efficiencies of 3 and 4 are comparable with those reported for other catalysts for TH carried out with 2-propanol or glycerol as a H-source. 1, with a sulfur ligand, is more efficient than 2 (Se analog) for both SMC and the Sonogashira coupling. The activities of 3 and 4 for TH are in the order Se > S.

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Palladium(ii) complexes bearing the 1,2,3-triazole based organosulfur/ selenium ligand: synthesis, structure and applications in Heck and Suzuki–Miyaura coupling as a catalyst via palladium nanoparticles

Cited by 56 publications

References 70 publications

A new Pd(II) complex of a sulfur ylide; Synthesis, X-ray characterization, theoretical study and catalytic activity toward the Suzuki–Miyaura reaction

A new Pd(II) complex of a sulfur ylide; Synthesis, X-ray characterization, theoretical study and catalytic activity toward the Suzuki–Miyaura reaction

New hybrid materials based on the grafting of Pd(ii)-amino complexes on the graphitic surface of AC: preparation, structures and catalytic properties

‘Click’ generated 1,2,3-triazole based organosulfur/selenium ligands and their Pd(ii) and Ru(ii) complexes: their synthesis, structure and catalytic applications

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