Graphene oxide as a metal-free catalyst for oxidation of primary amines to nitriles by hypochlorite

Primo, Ana; Puche, Marta; Pavel, Octavian Dumitru; Cojocaru, Bogdan; Tîrşoaga, Alina; Pârvulescu, Vasile I.; Garcı́a, Hermenegildo

doi:10.1039/c5cc09463a

Cited by 46 publications

(30 citation statements)

References 12 publications

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“…The Gs employed in the present work include rGO and GO. These materials have been reported previously and characterized fully . In particular, GO was obtained by the Hummers oxidation of graphite followed by exfoliation, and rGO was produced by thermal reduction of GO at 200 °C.…”

Section: Methodsmentioning

confidence: 99%

Reduced Graphene Oxide as a Metal‐Free Catalyst for the Light‐Assisted Fenton‐Like Reaction

et al. 2016

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Section: Methodsmentioning

confidence: 99%

Reduced Graphene Oxide as a Metal‐Free Catalyst for the Light‐Assisted Fenton‐Like Reaction

et al. 2016

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“…This NO 2 can then react with H 2 O, thereby leading to the formation of HNO 2 , which can act as an effective oxidant. The use of NaClO as oxidant and GnO as carbocatalyst has recently been reported for the conversion of primary amines into the corresponding nitriles …”

Section: Activation Of Oxidants and Reductants On Carbocatalystsmentioning

confidence: 99%

Carbocatalysis in Liquid‐Phase Reactions

et al. 2016

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There is broad interest in metal-free catalysis for sustainable chemistry. Carbocatalysis is a "green" option for catalytic transformations in the gas phase as well as in the liquid phase. This is evident by the numerous reports on gas-phase dehydrogenation and selective oxidation where carbon can be used as a successful alternative to metal oxide systems. Carbocatalysis for liquid-phase reactions, especially for organic synthesis, is an emerging research discipline and has undergone rapid development in recent years. This Review provides a critical analysis on the state-of-the-art of carbocatalysts for liquid-phase reactions, with a focus on the underlying mechanisms as well as the advantages and limitations of metal-free carbocatalysts.

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“…[47] Controlo ver the selectivity is an important issue when considering the amine/nitrile pair as ap romising candidate for LOHC.I th as been described that N-heterocycles are consideredg ood LOHCsa nd control of the selectivity can be easily achieved. In the case of tetradecylamine, hexadecylamine, and octadecylamine,t he only product ob- www.chemeurj.org served was the nitrile compound.…”

Section: Catalytic Propertiesmentioning

confidence: 99%

“…The use of long-chain alkylamines to control the selectivity in the oxidation of primary amines has recently been described. [47] Controlo ver the selectivity is an important issue when considering the amine/nitrile pair as ap romising candidate for LOHC.I th as been described that N-heterocycles are consideredg ood LOHCsa nd control of the selectivity can be easily achieved. For comparative purposes, we studied the activity of the ruthenium complexes in the dehydrogenation of indoline (Scheme 3).…”

Section: Catalytic Propertiesmentioning

confidence: 99%

Catalytic Hydrogen Production by Ruthenium Complexes from the Conversion of Primary Amines to Nitriles: Potential Application as a Liquid Organic Hydrogen Carrier

Ventura‐Espinosa

Marzá-Beltrán

Mata

2016

Chemistry A European J

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The potential application of the primary amine/nitrile pair as a liquid organic hydrogen carrier (LOHC) has been evaluated. Ruthenium complexes of formula [(p-cym)Ru(NHC)Cl ] (NHC=N-heterocyclic carbene) catalyze the acceptorless dehydrogenation of primary amines to nitriles with the formation of molecular hydrogen. Notably, the reaction proceeds without any external additive, under air, and under mild reaction conditions. The catalytic properties of a ruthenium complex supported on the surface of graphene have been explored for reutilization purposes. The ruthenium-supported catalyst is active for at least 10 runs without any apparent loss of activity. The results obtained in terms of catalytic activity, stability, and recyclability are encouraging for the potential application of the amine/nitrile pair as a LOHC. The main challenge in the dehydrogenation of benzylamines is the selectivity control, such as avoiding the formation of imine byproducts due to transamination reactions. Herein, selectivity has been achieved by using long-chain primary amines such as dodecylamine. Mechanistic studies have been performed to rationalize the key factors involved in the activity and selectivity of the catalysts in the dehydrogenation of amines. The experimental results suggest that the catalyst resting state contains a coordinated amine.

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Graphene oxide as a metal-free catalyst for oxidation of primary amines to nitriles by hypochlorite

Cited by 46 publications

References 12 publications

Reduced Graphene Oxide as a Metal‐Free Catalyst for the Light‐Assisted Fenton‐Like Reaction

Reduced Graphene Oxide as a Metal‐Free Catalyst for the Light‐Assisted Fenton‐Like Reaction

Carbocatalysis in Liquid‐Phase Reactions

Catalytic Hydrogen Production by Ruthenium Complexes from the Conversion of Primary Amines to Nitriles: Potential Application as a Liquid Organic Hydrogen Carrier

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