Iron‐Catalysed Reduction of Olefins using a Borohydride Reagent

Carter, Tom S.; Guiet, Léa; Frank, Dominik J.; West, J. Jason; Thomas, Stephen P.

doi:10.1002/adsc.201200577

Cited by 26 publications

(8 citation statements)

References 71 publications

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“…The yields of the reduced compounds were determined by 1 H NMR. All hydrogenated compounds are well‐known compounds in the literature and their characterization data were in a good agreement with literature …”

Section: Methodssupporting

confidence: 85%

Monodisperse CuPt alloy nanoparticles assembled on reduced graphene oxide as catalysts in the transfer hydrogenation of various functional organic groups

Ganjehyan

Nişancı²,

Sevim

et al. 2019

Applied Organom Chemis

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We present herein a new nanocatalyst, namely binary CuPt alloy nanoparticles (NPs) supported on reduced graphene oxide (CuPt‐rGO), as a highly active heterogeneous catalyst for the transfer hydrogenation (TH) protocol that is demonstrated to be applicable over the reduction of various unsaturated organic compounds (olefins, aldehydes/ketones and nitroarenes) in aqueous solutions at room temperature. CuPt alloy NPs were synthesized by the co‐reduction of metal (II) acetylacetonates by borane‐tert‐butylamine (BTB) complex in hot oleylamine (OAm) solution and then assembled on reduced graphene oxide (rGO) via ultrasonic‐assisted liquid phase self‐assembly method. The structure of yielded CuPt NPs and CuPt‐rGO nanocatalyst were characterized by TEM, XRD and ICP‐MS. The activity of Cu7Pt3‐rGO nanocatalysts were then tested for the THs that were conducted in a commercially available high‐pressure tube using water as sole solvent and ammonia borane as a hydrogen donor at room temperature. The presented catalytic TH protocol was successfully applied over nitroarenes, olefines and aldehydes/ketones, and all the tested compounds were converted to corresponding reduction products with the yields reaching up to 99% under ambient conditions. Moreover, the Cu7Pt3‐rGO nanocatalyst was also reusable in the TH by providing 99% yield after five consecutive runs in TH of nitrobenzene as an example.

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Section: Methodssupporting

confidence: 85%

Monodisperse CuPt alloy nanoparticles assembled on reduced graphene oxide as catalysts in the transfer hydrogenation of various functional organic groups

Ganjehyan

Nişancı²,

Sevim

et al. 2019

Applied Organom Chemis

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“…After 2 days for 4-methoxystyrene (91% conversion) or 8 days for 3,3-dimethylbut-1-ene (88% conversion), 4ethylanisole or 2,2-dimethylbutane was formed in 95% (TON = 17) or ∼100% (TON = 18) NMR yield, respectively, based on the conversion of the alkene. The products were identified by comparing the 1 H and 13 C NMR spectroscopic data with those from the literature for 4ethylanisole 22 or those of the authentic sample for 2,2-dimethylbutane.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Synthesis of Ruthenium Complexes with a Nonspectator Si,O,P-Chelate Ligand: Interconversion between a Hydrido(η²-silane) Complex and a Silyl Complex Leading to Catalytic Alkene Hydrogenation

et al. 2015

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A ruthenium complex bearing a new phosphine(η2-silane) chelate ligand connected by a xanthene backbone, Ru{κ4(Si,H,O,P)- t Bu2xantSiP(H)}(H)Cl(PPh3) (2), was synthesized by a ligand substitution reaction of Ru(H)Cl(PPh3)3 with 2,7-di-tert-butyl-4-dimethylsilyl-5-diphenylphosphino-9,9-dimethylxanthene (1, t Bu2xantSiP(H)). Dehydrogenation reaction of 2 with styrene, a hydrogen acceptor, gave a 16-electron phosphine(silyl) complex Ru{κ3(Si,O,P)- t Bu2xantSiP}Cl(PPh3) (3) together with ethylbenzene. Complex 2 was reproduced quantitatively by exposure of 3 to H2 (1 atm) at room temperature. Thus, hydrido(η2-silane) complex 2 and silyl complex 3 are interconvertible through alkene hydrogenation (from 2 to 3) and dihydrogen addition to the Ru–Si bond (from 3 to 2) in which t Bu2xantSiP functions as a nonspectator ligand by reversibly releasing and accommodating a hydrogen atom. Complex 2 was also found to catalyze hydrogenation of alkenes via this interconversion.

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“…42 Thomas has since reported in situ activation of iron dihalide complexes with i PrMgCl for the hydrogenation of a host of alkenes under 50 bar of H 2 43 or using borohydride reductants. 44 To date, no asymmetric, iron-catalyzed alkene hydrogenation that yields alkanes with a synthetically useful enantiomeric excess has been reported. On the basis of our recent findings in cobalt chemistry, we sought to develop iron precursors compatible with high-throughput experimentation for the evaluation of libraries of chiral bidentate phosphines.…”

Section: ■ Introductionmentioning

confidence: 99%

Synthesis and Hydrogenation Activity of Iron Dialkyl Complexes with Chiral Bidentate Phosphines

et al. 2014

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The activity of bis(phosphine) iron dialkyl complexes for the asymmetric hydrogenation of alkenes has been evaluated. High-throughput experimentation was used to identify suitable iron−phosphine combinations using the displacement of pyridine from py 2 Fe(CH 2 SiMe 3 ) 2 for precatalyst formation. Preparative-scale synthesis of a family of bis(phosphine) iron dialkyl complexes was also achieved using both ligand substitution and salt metathesis methods. Each of the isolated organometallic iron complexes was established as a tetrahedral and hence high-spin ferrous compound, as determined by Mossbauer spectroscopy, magnetic measurements, and, in many cases, X-ray diffraction. One example containing a Josiphos-type ligand, (SL-J212-1)Fe(CH 2 SiMe 3 ) 2 , proved more active than other isolated iron dialkyl precatalysts. Filtration experiments and the lack of observed enantioselectivity support dissociation of the phosphine ligand upon activation with dihydrogen and formation of catalytically active heterogeneous iron. The larger six-membered chelate is believed to reduce the coordination affinity of the phosphine for the iron center, enabling metal particle formation.

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Iron‐Catalysed Reduction of Olefins using a Borohydride Reagent

Cited by 26 publications

References 71 publications

Monodisperse CuPt alloy nanoparticles assembled on reduced graphene oxide as catalysts in the transfer hydrogenation of various functional organic groups

Monodisperse CuPt alloy nanoparticles assembled on reduced graphene oxide as catalysts in the transfer hydrogenation of various functional organic groups

Synthesis of Ruthenium Complexes with a Nonspectator Si,O,P-Chelate Ligand: Interconversion between a Hydrido(η²-silane) Complex and a Silyl Complex Leading to Catalytic Alkene Hydrogenation

Synthesis and Hydrogenation Activity of Iron Dialkyl Complexes with Chiral Bidentate Phosphines

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Iron‐Catalysed Reduction of Olefins using a Borohydride Reagent

Cited by 26 publications

References 71 publications

Monodisperse CuPt alloy nanoparticles assembled on reduced graphene oxide as catalysts in the transfer hydrogenation of various functional organic groups

Monodisperse CuPt alloy nanoparticles assembled on reduced graphene oxide as catalysts in the transfer hydrogenation of various functional organic groups

Synthesis of Ruthenium Complexes with a Nonspectator Si,O,P-Chelate Ligand: Interconversion between a Hydrido(η2-silane) Complex and a Silyl Complex Leading to Catalytic Alkene Hydrogenation

Synthesis and Hydrogenation Activity of Iron Dialkyl Complexes with Chiral Bidentate Phosphines

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Synthesis of Ruthenium Complexes with a Nonspectator Si,O,P-Chelate Ligand: Interconversion between a Hydrido(η²-silane) Complex and a Silyl Complex Leading to Catalytic Alkene Hydrogenation