Selectivity matters: Graphene oxide-mediated oxidative coupling of benzylamine to N‑benzylidine-1-phenylmethanamine under microwave irradiation

Bermúdez, J.M.; Menéndez, J.Á.; Arenillas, A.; Martínez‐Palou, Rafael; Romero, Antonio A.; Luque, Rafael

doi:10.1016/j.molcata.2015.05.010

Cited by 14 publications

(7 citation statements)

References 39 publications

(52 reference statements)

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“…3.5.1 Oxidative coupling. Oxidative coupling is used to produce a variety of important chemicals, such as imines for the synthesis of nitrogen-containing compounds for the biological and pharmaceutical fields, 162 while the oxidative coupling of methane (OCM) followed by oligomerisation has been proposed as a means to exploit stranded natural gas fields. 163 These reactions are typically catalysed by transition metals, but carbon-based catalysts have also found applications in this area.…”

Section: Other Reactionsmentioning

confidence: 99%

Things go better with coke: the beneficial role of carbonaceous deposits in heterogeneous catalysis

Collett

McGregor

2016

Catal. Sci. Technol.

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Section: Other Reactionsmentioning

confidence: 99%

Things go better with coke: the beneficial role of carbonaceous deposits in heterogeneous catalysis

Collett

McGregor

2016

Catal. Sci. Technol.

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“…In addition, Bermudez and co-workers report that hydrogen peroxide (H 2 O 2 ) acts as the oxidant for GO-catalyzed oxidation of amines and reveal the impact of H 2 O 2 and GO on the selectivity of various products. However, the reaction mechanism, including the effect of the free radical, is ambiguous . So far, the mechanism of amine oxidation catalyzed by carbocatalysts, which is vital for the catalyst design and their efficiency, still hangs in doubt.…”

Section: Introductionmentioning

confidence: 99%

“…However, the reaction mechanism, including the effect of the free radical, is ambiguous. 26 So far, the mechanism of amine oxidation catalyzed by carbocatalysts, which is vital for the catalyst design and their efficiency, still hangs in doubt.…”

Section: Introductionmentioning

confidence: 99%

Bifunctional Graphene-Based Metal-Free Catalysts for Oxidative Coupling of Amines

et al. 2019

ACS Appl. Mater. Interfaces

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Graphene oxide (GO), an emerging material ornamented with oxygen-containing functional groups, is becoming a promising alternative for various applications. The piranha solution treatment of GO can increase oxygen-containing functional groups and result in improved graphene oxide (IGO), as well as restore the functional groups lost because of the reaction. It is found that GO can oxidize the amine to the corresponding imine in the absence of oxygen and a catalyst, and the obtained IGO even shows higher activity. In addition, the piranha solution can partially restore the reactivity of GO after the reaction. The different roles of oxygen-containing functional groups in the oxidative coupling reaction are investigated. A possible reaction mechanism for the oxidation of benzylamine to N-benzylidene benzylamine is also proposed.

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“…In the event of the selective oxidation of amines using light as a clean and renewable energy resource, some advances has been achieved using heterogeneous catalysts, − but for the direct synthesis of imines from benzylamines, the use of CPs and MOFs as catalysts appears to have been rarely studied. − …”

Section: Introductionmentioning

confidence: 99%

Efficient Rare-Earth-Based Coordination Polymers as Green Photocatalysts for the Synthesis of Imines at Room Temperature

et al. 2018

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Five new rare-earth coordination polymers (CPs) were designed in order to offer a remarkable platform that contains light-harvesting antennas and catalytic active centers to achieve solar-energy conversion as green alternatives in the synthesis of imines. These five new spirobifluorene-containing Ln-CPs, named [Er(Hsfdc)(sfdc)(HO)]· xHO (RPF-30-Er), [Ln(Hsfdc)(sfdc)(EtOH)]·S (RPF-31-Ln, where Ln = La, Nd, and Sm and S = HO or EtOH), and [Ho(Hsfdc)(sfdc)(HO)] (RPF-32-Ho) (RPF = rare-earth polymeric framework and Hsfdc = 9,9'-spirobi[9 H-fluorene]-2,2'-dicarboxylic acid), have been solvothermally synthesized, and their structural features can be described as follows: (i) RPF-30-Er shows a 3D framework in which the inorganic trimers (secondary building units) are cross-linked by Hsfdc and sfdc linkers displaying a pcu topology. (ii) The isostructural RPF-31-Ln series of materials, together with RPF-32-Ho, exhibit a 1D network of chains growing along the a axis with a ribbon-of-rings topology type. The photocatalytic activity of the RPF- n materials was tested in the oxidative coupling of amines using molecular oxygen and air as oxidizing agents under warm light. Among the materials investigated, RPF-31-Nd was chosen to further investigate the approach in the selectivity of different amine derivates.

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Selectivity matters: Graphene oxide-mediated oxidative coupling of benzylamine to N‑benzylidine-1-phenylmethanamine under microwave irradiation

Cited by 14 publications

References 39 publications

Things go better with coke: the beneficial role of carbonaceous deposits in heterogeneous catalysis

Things go better with coke: the beneficial role of carbonaceous deposits in heterogeneous catalysis

Bifunctional Graphene-Based Metal-Free Catalysts for Oxidative Coupling of Amines

Efficient Rare-Earth-Based Coordination Polymers as Green Photocatalysts for the Synthesis of Imines at Room Temperature

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