Rapid one-pot propargylamine synthesis by plasmon mediated catalysis with gold nanoparticles on ZnO under ambient conditions

González‐Béjar, María; Peters, Kate M.; Hallett-Tapley, Geniece L.; Grenier, Michel; Scaiano, Juan C.

doi:10.1039/c3cc38287g

Cited by 80 publications

(51 citation statements)

References 68 publications

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“…Similar experimental conditions were adopted for the catalytic oxidation of 9-anthraldehyde in acetonitrile, yielding exclusively acetophenone (~80% yield) [132]. Coupling of an aldehyde (isovaler-aldehyde), an amine (piperidine) and an alkyne (phenylacetylene) to produce proparglyamine, molecules of pharmaceutical relevance, has been achieved under 530 nm irradiation of Au NPs supported on ZnO [133]. Enhanced selectivity compared with the pure thermal counterpart reaction has also been reported for the reduction of nitrobenzene to azobenzene on Au/ZrO 2 .…”

Section: Direct Plasmonic Photocatalysismentioning

confidence: 99%

Solar-Powered Plasmon-Enhanced Heterogeneous Catalysis

et al. 2016

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Photocatalysis uses semiconductors to convert sunlight into chemical energy. Recent reports have shown that plasmonic nanostructures can be used to extend semiconductor light absorption or to drive direct photocatalysis with visible light at their surface. In this review, we discuss the fundamental decay pathway of localized surface plasmons in the context of driving solar-powered chemical reactions. We also review different nanophotonic approaches demonstrated for increasing solar-tohydrogen conversion in photoelectrochemical water splitting, including experimental observations of enhanced reaction selectivity for reactions occurring at the metalsemiconductor interface. The enhanced reaction selectivity is highly dependent on the morphology, electronic properties, and spatial arrangement of composite nanostructures and their elements. In addition, we report on the particular features of photocatalytic reactions evolving at plasmonic metal surfaces and discuss the possibility of manipulating the reaction selectivity through the activation of targeted molecular bonds. Finally, using solar-tohydrogen conversion techniques as an example, we quantify the efficacy metrics achievable in plasmon-driven photoelectrochemical systems and highlight some of the new directions that could lead to the practical implementation of solar-powered plasmon-based catalytic devices.

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Section: Direct Plasmonic Photocatalysismentioning

confidence: 99%

Solar-Powered Plasmon-Enhanced Heterogeneous Catalysis

et al. 2016

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“…Interestingly, it has been recently demonstrated that the SPR excitation in plasmonic nanoparticles can be put to work to enhance and/or mediate catalytic processes at the surface in so‐called SPR‐enhanced or SPR‐mediated catalysis. This can occur through charge transfer of SPR‐excited hot electrons at the metal/molecule interface, local heating, and as a result of the antenna effect 14–16. However, in catalytic applications, nanoparticles frequently undergo aggregation and/or dissolution, which hampers their stability 17.…”

Section: Introductionmentioning

confidence: 99%

Probing the Catalytic Activity of Reduced Graphene Oxide Decorated with Au Nanoparticles Triggered by Visible Light

Wang

Trindade

Aquino

et al. 2015

Chemistry A European J

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Hybrid materials in which reduced graphene oxide (rGO) is decorated with Au nanoparticles (rGO-Au NPs) were obtained by the in situ reduction of GO and AuCl4(-)(aq) by ascorbic acid. On laser excitation, rGO could be oxidized as a result of the surface plasmon resonance (SPR) excitation in the Au NPs, which generates activated O2 through the transfer of SPR-excited hot electrons to O2 molecules adsorbed from air. The SPR-mediated catalytic oxidation of p-aminothiophenol (PATP) to p,p'-dimercaptoazobenzene (DMAB) was then employed as a model reaction to probe the effect of rGO as a support for Au NPs on their SPR-mediated catalytic activities. The increased conversion of PATP to DMAB relative to individual Au NPs indicated that charge-transfer processes from rGO to Au took place and contributed to improved SPR-mediated activity. Since the transfer of electrons from Au to adsorbed O2 molecules is the crucial step for PATP oxidation, in addition to the SPR-excited hot electrons of Au NPs, the transfer of electrons from rGO to Au contributed to increasing the electron density of Au above the Fermi level and thus the Au-to-O2 charge-transfer process.

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“…141 Interaction of the supporter and phenylacetylene is a necessary condition for high yield of propargylamines. Compared with TiO2 and Al2O3 as the supporters, the interaction between ZnO and phenylacetylene is stronger which is more favourable for the adsorption of phenylacetylene.…”

Section: Scheme 41mentioning

confidence: 99%

The application of heterogeneous visible light photocatalysts in organic synthesis

Chen

Cen

et al. 2016

Catal. Sci. Technol.

219

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The advantage of visible-light photocatalysis lies in its use of clean, renewable, cheap visible light as a driving force. Recently heterogeneous visible light photocatalysts have drawn much attention due to their nature of easy recycling and simple chemical work-up. Immense effort has been devoted to the application of solar energy in the field of energy regeneration such as hydrogen production and reduction of carbon dioxide. Recently the solar energy also has captured much attention in organic synthesis due to its unique advantages. This paper will review the state-of-the-art progresses in the application of heterogeneous visible-light photocatalysis in organic synthesis through four sections: oxidation of alcohols, oxidation of amines, carbon-carbon bond formation reactions, and carbon-hetero bond formation reactions.

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Rapid one-pot propargylamine synthesis by plasmon mediated catalysis with gold nanoparticles on ZnO under ambient conditions

Cited by 80 publications

References 68 publications

Solar-Powered Plasmon-Enhanced Heterogeneous Catalysis

Solar-Powered Plasmon-Enhanced Heterogeneous Catalysis

Probing the Catalytic Activity of Reduced Graphene Oxide Decorated with Au Nanoparticles Triggered by Visible Light

The application of heterogeneous visible light photocatalysts in organic synthesis

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