90200-72-9Relevant academic research and scientific papers
Chemoselective and Tandem Reduction of Arenes Using a Metal–Organic Framework-Supported Single-Site Cobalt Catalyst
Antil, Neha,Kumar, Ajay,Akhtar, Naved,Begum, Wahida,Chauhan, Manav,Newar, Rajashree,Rawat, Manhar Singh,Manna, Kuntal
supporting information, p. 1031 - 1040 (2022/01/19)
The development of heterogeneous, chemoselective, and tandem catalytic systems using abundant metals is vital for the sustainable synthesis of fine and commodity chemicals. We report a robust and recyclable single-site cobalt-hydride catalyst based on a porous aluminum metal–organic framework (DUT-5 MOF) for chemoselective hydrogenation of arenes. The DUT-5 node-supported cobalt(II) hydride (DUT-5-CoH) is a versatile solid catalyst for chemoselective hydrogenation of a range of nonpolar and polar arenes, including heteroarenes such as pyridines, quinolines, isoquinolines, indoles, and furans to afford cycloalkanes and saturated heterocycles in excellent yields. DUT-5-CoH exhibited excellent functional group tolerance and could be reusable at least five times without decreased activity. The same MOF-Co catalyst was also efficient for tandem hydrogenation–hydrodeoxygenation of aryl carbonyl compounds, including biomass-derived platform molecules such as furfural and hydroxymethylfurfural to cycloalkanes. In the case of hydrogenation of cumene, our spectroscopic, kinetic, and density functional theory (DFT) studies suggest the insertion of a trisubstituted alkene intermediate into the Co–H bond occurring in the turnover limiting step. Our work highlights the potential of MOF-supported single-site base–metal catalysts for sustainable and environment-friendly industrial production of chemicals and biofuels.
Palladium-Catalyzed Reductive Insertion of Alcohols into Aryl Ether Bonds
Wang, Meng,Gutiérrez, Oliver Y.,Camaioni, Donald M.,Lercher, Johannes A.
supporting information, p. 3747 - 3751 (2018/03/21)
Palladium on carbon catalyzes C?O bond cleavage of aryl ethers (diphenyl ether and cyclohexyl phenyl ether) by alcohols (R?OH) in H2. The aromatic C?O bond is cleaved by reductive solvolysis, which is initiated by Pd-catalyzed partial hydrogenation of one phenyl ring to form an enol ether. The enol ether reacts rapidly with alcohols to form a ketal, which generates 1-cyclohexenyl?O?R by eliminating phenol or an alkanol. Subsequent hydrogenation leads to cyclohexyl?O?R.
Ruthenium nanoparticles supported on multi-walled carbon nanotubes: Highly effective catalytic system for hydrogenation processes
Jahjah, Mohamad,Kihn, Yolande,Teuma, Emmanuelle,Gómez, Montserrat
experimental part, p. 106 - 112 (2010/12/25)
Immobilization of small and homogeneously dispersed ruthenium nanoparticles stabilized by 4-(3-phenylpropyl)pyridine ligand (RuL) on functionalized multi-walled carbon nanotubes (RuL-MWCNT) have been prepared and characterized by elemental analysis and transmission electronic microscopy. A comparative hydrogenation study of unsaturated substrates using non-supported (RuL) and supported catalytic systems (RuL-MWCNT) was carried out. For all the substrates, the activity of the supported catalyst was higher towards the full hydrogenated product than that obtained using the non-supported one. Moreover, the catalytic effect of the support nature was studied using RuL immobilized on silica (RuL-SiO2), alumina (RuL-Al2O3) and activated carbon (RuL-AC). The best activities and selectivities were found for RuL-MWCNT system, maintaining its catalytic behaviour upon recycling.
Synthesis, characterization and catalytic reactivity of ruthenium nanoparticles stabilized by chiral N-donor ligands
Jansat, Susanna,Picurelli, David,Pelzer, Katrin,Philippot, Karine,Gomez, Montserrat,Muller, Guillermo,Lecante, Pierre,Chaudret, Bruno
, p. 115 - 122 (2007/10/03)
The decomposition of the organometallic precursor [Ru(cod)(cot)] (cod = 1,5-cyclooctadiene; cot = 1,3,5-cyclooctatriene) under mild conditions (room temperature, 3 bars H2) and in the presence of optically pure ligands, L*, namely (R)-2-aminobutanol 1, amino(oxazolines) (2, 3), hydroxy(oxazoline) (4) and bis(oxazolines) (5-8), leads to stable ruthenium nanoparticles exhibiting a mean diameter between 1.6-2.5 nm. These nanoparticles can be isolated and re-dispersed. They display different mean sizes, shapes and dispersions depending on the stabilizer nature. These new colloids (Ru1-Ru18) have been characterized by both solid state and molecular chemistry techniques, including TEM/HRTEM, WAXS, elemental analysis, and IR and NMR spectroscopy. To further characterize the surface state of these particles, their catalytic behaviour has been examined in the reduction of organic prochiral unsaturated substrates. Although the asymmetric induction obtained is modest, it reveals the influence of the asymmetric ligand coordinated at the surface of the particles. the Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2006.
A simple and reproducible method for the synthesis of silica-supported rhodium nanoparticles and their investigation in the hydrogenation of aromatic compounds
Mevellec, Vincent,Nowicki, Audrey,Roucoux, Alain,Dujardin, Christophe,Granger, Pascal,Payen, Edmond,Philippot, Karine
, p. 1214 - 1219 (2007/10/03)
Colloidal suspensions of rhodium nanoparticles have been easily prepared in aqueous solution by chemical reduction of the precursor RhCl 3·3H2O in the presence of the surfactant N,N-dimethyl-N-cetyl-N-(2-hydroxyethyl)ammonium chloride (HEA16Cl) and further used to immobilize rhodium nanoparticles on silica by simple impregnation. The obtained silica-supported rhodium nanoparticles have been investigated by adapted characterization methods such as transmission electron microscopy and X-ray photoelectron spectroscopy. A particle size increase from 2.4 to 5 nm after the silica immobilization step and total elimination of the surfactant has been observed. This "heterogeneous" catalyst displayed good activities for the hydrogenation of mono-, di- alkylsubstituted and/or functionalized aromatic derivatives in water under atmospheric hydrogen pressure and at room temperature. In all cases, the catalyst could be recovered several times after a simple decantation or filtration and reused without any significant loss in catalytic activity. This supported catalyst has also been tested under higher hydrogen pressure giving rise to TOFs reaching 6430 h -1 at 30 bar and in terms of catalytic lifetime 30 000 TTO in 8.5 h for pure anisole hydrogenation at 40 bar. the Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2006.
