Gold nanoparticle-decorated reduced graphene oxide (rGO) as a highly reactive catalyst for the selective α,β-dehydrogenation of N-methyl-4-piperidone

Brenda Flore Kenyim; Mihir Tzalis; Marilyn Kaul; Robert Oestreich; Aysenur Limon; Chancellin Pecheu Nkepdep; Christoph Janiak

doi:10.3762/bxiv.2025.47.v1

Gold nanoparticle-decorated reduced graphene oxide (rGO) as a highly reactive catalyst for the selective α,β-dehydrogenation of N-methyl-4-piperidone

Brenda Flore Kenyim ,
Mihir Tzalis ,
Marilyn Kaul ,
Robert Oestreich ,
Aysenur Limon ,
Chancellin Pecheu Nkepdep and
Christoph Janiak

Submitting author affiliation:

Heinrich-Heine-Universität Düsseldorf, Düsseldorf, Germany

Beilstein Arch. 2025, 202547. https://doi.org/10.3762/bxiv.2025.47.v1

Published 17 Jul 2025

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Show All Preprints Nanotechnology Organic chemistry Bioorganic chemistry / chemical biology Catalysis Chemical methods and reactions Flow and process chemistry Green and sustainable chemistry Materials chemistry Medicinal and pharmaceutical chemistry Nano- and molecular-scale electronics Nano-biomaterials and bioscience Nano-optics Nanomagnetics Nanomaterials, thin films and nanointerfaces Nanomedicine Nanometrology and nanomechanics Nanopatterning, self-assembly and nanofabrication Nanostructures for energy and sensing applications Natural products chemistry Organo main group chemistry Other nanotechnology (unclassified) Other organic chemistry (unclassified) Photochemistry and photovoltaics Physical organic chemistry Supramolecular chemistry

Abstract

Gold nanoparticles (AuNPs) supported on reduced graphene oxide (AuNPs/rGO) were demonstrated to be a highly reactive catalyst for the selective α, β-oxidative dehydrogenation (ODH) of N-methyl-4-piperidone as a model substrate for β-N-substituted saturated ketones. This substrate was chosen due to the significant pharmaceutical relevance of the reaction product 1-methyl-2,3-dihydropyridin-4(1H)-one which is very expensive (>1000 €/g), in contrast to the inexpensive starting material (0.15 €/g). Various synthesis methods were employed to prepare AuNPs supported on different carbon materials, including reduced graphene oxide (rGO), activated carbon (AC), and carbon black (CB), to investigate the influence of the carbon support on the catalyst performance. As stabilizing agents for the AuNPs citrate (Cit) and the polyoxometallate [SiW₉O₃₄]^10– (SiW₉) were used. Among the tested catalysts, the rGO-supported ones, Au-Cit/rGO, Au-SiW₉/rGO, Au@SiW₉/rGO and exhibited superior catalytic activity for the selective oxidation reaction. These findings offer valuable insights for the design of highly active Au-based catalysts for the dehydrogenation of β-N-substituted saturated ketones and other fine chemical applications.

Keywords: Supported gold nanoparticles; Oxidative dehydrogenation; Reduced graphene oxide; β-N-substituted ketones

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Kenyim, B. F.; Tzalis, M.; Kaul, M.; Oestreich, R.; Limon, A.; Pecheu Nkepdep, C.; Janiak, C. Beilstein Arch. 2025, 202547. doi:10.3762/bxiv.2025.47.v1

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aromatic	the word “aromatic”
aromatic aldehyde	the word “aromatic” OR “aldehyde”
+aromatic +aldehyde	both words “aromatic” AND “aldehyde”
+aromatic -aldehyde	the word “aromatic” but NOT “aldehyde”
“aromatic aldehyde”	the exact phrase “aromatic aldehyde”
benz*	words which begin with “benz”, such as “benzene” or “benzyl”
benz*yl	words that begin with “benz” and end with “yl”, such as “benzyl” or “benzoyl”
benzyl~	words that are close to the word “benzyl”, such as “benzoyl” (i.e., fuzzy search)