Rhodium/Graphite-Catalyzed Hydrogenation of Carbocyclic and Heterocyclic Aromatic Compounds

Falini, Giuseppe; Gualandi, Andrea; Savoia, Diego

doi:10.1055/s-0029-1216852

Cited by 6 publications

(1 citation statement)

References 8 publications

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“…One solution to the aforementioned problem is to exploit the high activity of nanoscaled transition metal catalysts. Several groups have achieved arene hydrogenation under ambient pressure and temperature using various transition metal nanostructures, which include Pt nanowires, Rh nanoparticles, − and Ru–Pt, Rh–Pd, Rh–Ir, Rh–Pt, , and Ir–Pt bimetallic nanoparticles. However, preparation of these catalysts usually involves tedious steps and is inconvenient for organic chemists.…”

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confidence: 99%

Arene Reduction by Rh/Pd or Rh/Pt under 1 atm Hydrogen Gas and Room Temperature

Li,

2024

Org. Lett.

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Current methods for arene hydrogenation generally need either harsh reaction conditions or complex catalyst preparation.Here we describe a mild and convenient protocol that only utilizes commercially available catalysts. Using [Rh(nbd)Cl] 2 and Pd/C together as catalysts, arenes bearing various functional groups can be hydrogenated under 1 atm of H 2 at room temperature. This arene hydrogenation can also be achieved using catalysts of [Rh(cod)Cl] 2 and PtO 2 , thus avoiding glovebox manipulations and simplifying the reaction procedure.

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confidence: 99%

Arene Reduction by Rh/Pd or Rh/Pt under 1 atm Hydrogen Gas and Room Temperature

Li,

2024

Org. Lett.

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Reaction Rate Acceleration of Cooperative Catalytic Systems: Metal Nanoparticles and Lewis Acids in Arene Hydrogenation

Miyamura

Kobayashi

2022

Angewandte Chemie

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Employing two distinct catalysts in one reaction medium synergistically is a powerful strategy for activating less reactive substrates. Although the approach has been well-developed in homogeneous conditions, it remains challenging and rare in heterogeneous catalysis, especially under gas-liquid-solid multiphase reaction conditions. Here, we describe the development of cooperative and synergistic catalyst systems of heterogeneous Rh-Pt bimetallic nanoparticle catalysts, Rh-Pt/DMPSi-Al 2 O 3 , and Sc(OTf) 3 in the liquid phase for the hydrogenation of arenes under very mild conditions. Dramatic rate acceleration was achieved with cooperative activation. Remarkably, more challenging substrates that contained strong electron-donating groups and sterically hindered substituents were smoothly hydrogenated. Mechanistic insights into the cooperative activation of an aromatic substrate by heterogeneous metal nanoparticles and a soluble Lewis acid was obtained by kinetic studies and by direct observation of 1 H and 45 Sc NMR spectra.

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Reaction Rate Acceleration of Cooperative Catalytic Systems: Metal Nanoparticles and Lewis Acids in Arene Hydrogenation

Miyamura

Kobayashi

2022

Angew Chem Int Ed

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Employing two distinct catalysts in one reaction medium synergistically is a powerful strategy for activating less reactive substrates. Although the approach has been well‐developed in homogeneous conditions, it remains challenging and rare in heterogeneous catalysis, especially under gas‐liquid‐solid multiphase reaction conditions. Here, we describe the development of cooperative and synergistic catalyst systems of heterogeneous Rh‐Pt bimetallic nanoparticle catalysts, Rh‐Pt/DMPSi‐Al2O3, and Sc(OTf)3 in the liquid phase for the hydrogenation of arenes under very mild conditions. Dramatic rate acceleration was achieved with cooperative activation. Remarkably, more challenging substrates that contained strong electron‐donating groups and sterically hindered substituents were smoothly hydrogenated. Mechanistic insights into the cooperative activation of an aromatic substrate by heterogeneous metal nanoparticles and a soluble Lewis acid was obtained by kinetic studies and by direct observation of 1H and 45Sc NMR spectra.

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Rhodium/Graphite-Catalyzed Hydrogenation of Carbocyclic and Heterocyclic Aromatic Compounds

Cited by 6 publications

References 8 publications

Arene Reduction by Rh/Pd or Rh/Pt under 1 atm Hydrogen Gas and Room Temperature

Arene Reduction by Rh/Pd or Rh/Pt under 1 atm Hydrogen Gas and Room Temperature

Reaction Rate Acceleration of Cooperative Catalytic Systems: Metal Nanoparticles and Lewis Acids in Arene Hydrogenation

Reaction Rate Acceleration of Cooperative Catalytic Systems: Metal Nanoparticles and Lewis Acids in Arene Hydrogenation

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