DNA‐Mediated Palladium Nanoparticles as an Efficient Catalyst for Hydrogenation‐ and Suzuki–Miyaura Coupling Reactions

Itoh, Hisanori; Maeda, Hironori; Yamada, S.; Hori, Yoji

doi:10.1002/cctc.201200351

Cited by 26 publications

(17 citation statements)

References 13 publications

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“…A new DNA‐based asymmetric Diels‐Alder,,, Friedel‐Crafts, or other C–C bond forming reactions, yielding desired products with 99% or 93% ee, have been performed by utilizing a DNA‐copper catalyst. DNA was also used to stabilize metal nanoparticles such as Rh,, Pt,, Fe, Au,,, Ag,, Pd,, or Re ,…”

Section: Introductionmentioning

confidence: 99%

Rh/DNA Nanoparticles, Synthesis, Characterization and Catalytic Activity in “On Water” Asymmetric Hydroformylation Reaction

Alsalahi

Trzeciak

2018

ChemistrySelect

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DNA-stabilized Rh NPs were synthesized by the chemical reduction of Rh(acac)(CO) 2 (acac = acetylacetonate) in water at 80 8C. The obtained nanoparticles, Rh/DNA, were characterized by various spectroscopic and microscopic methods, such as IR, UV-Vis, XRD (X-ray diffraction), ICP-AES (Inductively coupled plasma atomic emission spectroscopy), EDX (Energy-dispersive X-ray spectroscopy analysis), TEM (Transmission electron microscopy), and SEM (Scanning electron microscopy) analyses. Their catalytic activity was successfully investigated in the "on water" hydroformylation of styrene. The conversion of styrene and chemoselectivity towards aldehydes were 100%. A high iso/n ratio was also obtained, up to 6.1 and 16.7 with PPh 3 (triphenylphosphine) and (R)-BINAP (2,2'-bis(diphenylphosphino)-1,1'-binaphthyl) ligands respectively. In the hydroformylation of vinyl acetate with Rh/DNA, performed in the presence of a chiral BINAP ligand "on water", high enantioselectivity was obtained, up to 49% ee. These results were significantly better than when utilizing Rh(acac)(CO) 2 as a catalyst under the same conditions. dd, 24.5 ppm, J Rh-P 129.6 Hz, J P-P 44.2 Hz; dd, 45.4 ppm, J Rh-P 161.1 Hz d, 36.3 ppm, J Rh-P 176.7 Hz d, 49 ppm, J Rh-P 176.7 Hz Rh(acac)(CO) 2 + BINAP + H 2 /CO + vinyl acetate (on water, Figure S10) d, 46.6 ppm, J Rh-P 172.6 Hz d, 53.1 ppm, J Rh-P 168.4 Hz Rh(acac)(CO) 2 + BINAP + H 2 /CO + vinyl acetate (in C 6 D 6 , Figure S27) 1) dd, 24.5 ppm, J Rh-P 141.2 Hz, J P-P 42 Hz; dd, 48.4 ppm, J Rh-P 152.2 Hz; 2) dd, 37.5 ppm, J P-P 32.3, J Rh-P 75.3 Hz m, 33.7 ppm, J Rh-P 68.7 Hz d, 36.6 ppm, J Rh-P 137.6 Rh/DNA + BINAP + H 2 /CO + vinyl acetate (Figure S8) 1) dd, 23.3 ppm, J Rh-P 134.5 Hz, J P-P 44.9 Hz; dd, 43.9 ppm, J Rh-P 155.6 Hz; 2) dd, 39.7 ppm, J P-P 44.9, J Rh-P 144.8 Hz m, 35.3 ppm, J Rh-P 75.3 Hz m, 12.2 ppm, J Rh-P 215.8 Hz d, 25.1 ppm, J Rh-P 139.2 Hz d, 28.9 ppm, J Rh-P 85 Hz m, 35.3 ppm, J Rh-P 75 Hz a experimental details are presented in supplementary material. Signals originated from BINAPO and BINAPO 2 were observed ca. 30 ppm and ca. À15 ppm. [77]

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Section: Introductionmentioning

confidence: 99%

Rh/DNA Nanoparticles, Synthesis, Characterization and Catalytic Activity in “On Water” Asymmetric Hydroformylation Reaction

Alsalahi

Trzeciak

2018

ChemistrySelect

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“…[29][30][31][32] Especially, stable colloidal Pd NPs supported by conventional and non-conventional supports have been exploited as catalysts for Suzuki cross coupling reactions. [33][34][35] In most of the cases the Pd NPs were synthesized by chemical, electrochemical or sonochemical methods, using dendrimers, polymers, or metalorganic frameworks as stabilizers. [36][37][38] Although, there are some reports on the green synthesis of Pd NPs using plant materials, e.g.…”

Section: Introductionmentioning

confidence: 99%

Biogenic synthesis of palladium nanoparticles using Pulicaria glutinosa extract and their catalytic activity towards the Suzuki coupling reaction

et al. 2014

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Green synthesis of nanomaterials finds the edge over chemical methods due to its environmental compatibility. Herein, we report a facile and eco-friendly method for the synthesis of palladium (Pd) nanoparticles (NPs) using an aqueous solution of Pulicaria glutinosa, a plant widely found in a large region of Saudi Arabia, as a bioreductant. The as-prepared Pd NPs were characterized using ultraviolet-visible (UV-vis) spectroscopy, powder X-ray diffraction (XRD), transmission electron microscopy (TEM), energy-dispersive X-ray spectroscopy (EDX), and Fourier transform-infrared spectroscopy (FT-IR). The hydroxyl groups of the plant extract (PE) molecules were found mainly responsible for the reduction and growth of Pd NPs. FT-IR analysis confirmed the dual role of the PE, both as a bioreductant as well as a capping ligand, which stabilizes the surface of Pd NPs. The crystalline nature of the Pd NPs was identified using XRD analysis which confirmed the formation of a face-centered cubic structure (JCPDS: 87-0641, space group: Fm3m (225)). Furthermore, the as-synthesized Pd NPs demonstrated excellent catalytic activity towards the Suzuki coupling reaction under aqueous and aerobic conditions. Kinetic studies of the catalytic reaction monitored using GC confirmed that the reaction completes in less than 5 minutes.

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“…But until now only one article has been published on testing DNA supported Pd NPs in Suzuki-Miyaura reaction. In this study low efficiency has been achieved with bromobenzene derivatives [31].…”

Section: Introductionmentioning

confidence: 95%

Pd/DNA as Highly Active and Recyclable Catalyst of Suzuki–Miyaura Coupling

2018

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Pd/DNA catalysts were prepared in a mixed H2O/EtOH solvent using palladium precursors, Pd(OAc)2 and PdCl2, in different dosages and salmon fish sperm DNA. As prepared, the Pd/DNA contained Pd(II) and Pd(0) nanoparticles of various sizes and morphologies, depending on the preparation method. Pd/DNA efficiently catalyzed the Suzuki–Miyaura cross-coupling of various aryl bromides with phenylboronic acids. The catalyst was recovered by simple phase separation and then reused in seven consecutive cycles with a high activity.

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DNA‐Mediated Palladium Nanoparticles as an Efficient Catalyst for Hydrogenation‐ and Suzuki–Miyaura Coupling Reactions

Abstract: Waste DNA gets a second life: A Pd/DNA catalyst, which was prepared by a facile method, has high activity for the selective hydrogenation of carboncarbon triple bonds, carbon–carbon double bonds, and nitro groups, as well as for the Suzuki–Miyaura coupling reaction.

Cited by 26 publications

References 13 publications

Rh/DNA Nanoparticles, Synthesis, Characterization and Catalytic Activity in “On Water” Asymmetric Hydroformylation Reaction

Rh/DNA Nanoparticles, Synthesis, Characterization and Catalytic Activity in “On Water” Asymmetric Hydroformylation Reaction

Biogenic synthesis of palladium nanoparticles using Pulicaria glutinosa extract and their catalytic activity towards the Suzuki coupling reaction

Pd/DNA as Highly Active and Recyclable Catalyst of Suzuki–Miyaura Coupling

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