Diphosphite ligands derived from carbohydrates as stabilizers for ruthenium nanoparticles: promising catalytic systems in arene hydrogenation

Gual, Aitor; Axet, M. Rosa; Philippot, Karine; Chaudret, Bruno; Denicourt‐Nowicki, Audrey; Roucoux, Alain; Castillón, Sergio; Claver, Carmen

doi:10.1039/b802316f

Cited by 72 publications

(43 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Small diameters and high reproducibility in the formation of metallic particles are related with the addition of stabilizers, which interacts with metal during its reduction to generate particular properties in the material, i.e. chiral surface in NPs with specific shape and composition [22][23][24][25][26][27][28][29] .…”

Section: Introductionmentioning

confidence: 99%

Silica Supported Rhodium Metal Nanoparticles Stabilized With (-)-Diop. Effect of Ligand Concentration and Metal Loading on the Enantioselective Hydrogenation of Ketones

Ruiz¹,

Mella²,

Fierro

et al. 2012

J. Chil. Chem. Soc.

View full text Add to dashboard Cite

Supported nanoparticles (NPs) in presence of chiral ligand (L) were synthesized for their use in enantioselective hydrogenation reactions. Catalysts were obtained by chemical reduction from rhodium chloride hydrate, RhCl 3 ×3H 2 O, in presence of (-)-DIOP ligand ((4R,5R)-4,5-Bis(diphenylphosphino-methyl)-2,2-dimethyl-1,3-dioxolane) that allows to control NPs growing and to obtain solids having chiral surfaces. Chirally stabilized rhodium NPs on SiO 2 were characterized using techniques such as: TEM, electron diffraction, EDS, nitrogen adsorption-desorption isotherms and XPS.This work includes the study of some variables such as metal loading and ligand concentration and their effect in metal core sizes, catalytic activity and enantioselectivity. Catalysts properties have also been evaluated in the hydrogenation of substrates: acetophenone (AP), 1-phenyl-1,2-propanedione (PPD), 3,4-hexanedione (HD), 2,3-butanedione (BD) and ethyl pyruvate (EP) as reaction test.Ligand plays a fundamental role in the synthesis of NPs and enantioselectivity in hydrogenations reactions. That is, due to it generates metal particle size < 5.8 nm compared with unstabilized systems that generate average diameter around 14 nm. Results indicate increased activity in catalytic systems obtained from the stabilization of NPs. Enantioselectivity levels reach values up to 53% due to the chiral ligand is on the catalysts surface.

show abstract

Section: Introductionmentioning

confidence: 99%

Silica Supported Rhodium Metal Nanoparticles Stabilized With (-)-Diop. Effect of Ligand Concentration and Metal Loading on the Enantioselective Hydrogenation of Ketones

Ruiz¹,

Mella²,

Fierro

et al. 2012

J. Chil. Chem. Soc.

View full text Add to dashboard Cite

show abstract

“…For this reason, Chaudret and co-workers have thoroughly developed the synthesis of Ru-NPs in organic solvents, usually tetrahydrofuran, from the decomposition of the organometallic precursor cyclooctadiene cyclooctatriene ruthenium, Ru(COD)(COT). In this work it has been thoroughly proven that the size, shape and nature of the Ru-NPs produced could be controlled by varying the support and/or capping agent [43][44][45][46][47].…”

Section: Synthesis and Characterisation Of Ru-nps In Ionic Liquidsmentioning

confidence: 99%

Ruthenium Nanoparticles in Ionic Liquids – A Saga

Campbell

Prechtl²,

Santini³

et al. 2013

COC

View full text Add to dashboard Cite

Ionic liquids (ILs) are excellent media for the generation and stabilisation of metallic nanoparticles (NPs). Their ionic character coupled with 3-D structural pre-organisation in the liquid state, serves to direct the growth of transition metal NPs generated in situ, and to subsequently protect and stabilise them. Until now, many different NPs have been successfully synthesised within these media, however much attention has been paid to Ru-NPs. These have been prepared with small sizes and narrow size distributions by reduction of organometallic compounds with molecular hydrogen as well as decomposition of transition-metal complexes in the zero-valent state. These stable Ru-NPs immobilised in the ILs have proven to be efficient green catalysts for several reactions in multiphase conditions, including important energy-related processes such as biomass refinement. Furthermore, they present potential novel materials for use in the production of smarter electronic devices. In this review, the synthesis, stabilisation and size-control of Ru-NPs via various methods in different ILs is discussed, followed by their varied application in catalysis and potential in new fields.

show abstract

“…Substrates and solvents used in this study were analytical grade and treated by standard methods 1,23,24 .…”

Section: Methodsmentioning

confidence: 99%

“…A few research groups have focused their studies in using chiral nanoparticles as catalysts. NPs have been also used as catalysts in reactions such as hydroformylation, allylic alkylation, hydrosilylations, Suzuki and Heck-type, couplings, among others achieving good results [19][20][21][22][23][24][25][26] .…”

Section: Introductionmentioning

confidence: 99%

CHIRAL Rh/SiO2 CATALYSTS FOR ENANTIOSELECTIVE HYDROGENATION REACTIONS: THE ROLE OF (S,S)-DIPAMP AS CHIRAL MODIFIER AND STABILIZER ON METALLIC NANOPARTICLES SYNTHESIS

Mella¹,

Ávila²,

SANCHEZ³

et al. 2013

J. Chil. Chem. Soc.

View full text Add to dashboard Cite

Rhodium nanoparticles were successfully stabilized by the (S,S)-1,2-ethanediylbis [(2-ethoxyphenyl)phenylphosphine] ((S,S)-DIPAMP) deposited on SiO 2 prepared by a facile reduction and impregnation method. The chiral catalysts obtained were efficient for the enantioselective hydrogenation reactions of prochiral compounds. The catalysts synthesized from [Rh(μ-OMe)(COD)] 2 in the presence of different amounts of a ligand used as chiral stabilizer, showed good metal dispersion. As shown by TEM, the metal particle size ranged between 1 and 2 nm using stabilizer and 9.1 nm was achieved without chiral ligand. Other techniques were used to characterize the chiral catalysts such as X-ray diffraction (XRD), electron diffraction, thermogravimetric analysis (TGA) and N 2 adsorption-desorption isotherms.(S,S)-DIPAMP was used as the stabilizer of metal particles to prevent growing and agglomeration, and it also acts as chiral modifier inducing enantioselectivity in the asymmetric hydrogenation of 3,4-hexanodione (HD), ethyl pyruvate (EP), ketopantolactone (KP), and acetophenone (AP). Under specific conditions such as 25 °C, 40 bar of H 2 and substrate/Rh=100, 1%Rh-(S,S)-DIPAMP/SiO 2 chiral catalysts showed excellent catalytic performance with conversion and enantiomeric excess (ee) levels up to 99% and 54% respectively.

show abstract

Diphosphite ligands derived from carbohydrates as stabilizers for ruthenium nanoparticles: promising catalytic systems in arene hydrogenation

Cited by 72 publications

References 19 publications

Silica Supported Rhodium Metal Nanoparticles Stabilized With (-)-Diop. Effect of Ligand Concentration and Metal Loading on the Enantioselective Hydrogenation of Ketones

Silica Supported Rhodium Metal Nanoparticles Stabilized With (-)-Diop. Effect of Ligand Concentration and Metal Loading on the Enantioselective Hydrogenation of Ketones

Ruthenium Nanoparticles in Ionic Liquids – A Saga

CHIRAL Rh/SiO2 CATALYSTS FOR ENANTIOSELECTIVE HYDROGENATION REACTIONS: THE ROLE OF (S,S)-DIPAMP AS CHIRAL MODIFIER AND STABILIZER ON METALLIC NANOPARTICLES SYNTHESIS

Contact Info

Product

Resources

About