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Open AccessFeature PaperArticle

Cross-Linked Cyclodextrins Bimetallic Nanocatalysts: Applications in Microwave-Assisted Reductive Aminations

1
Dipartimento di Scienza e Tecnologia del Farmaco and NIS—Centre for Nanostructured Interfaces and Surfaces, University of Turin, Via Giuria 9, 10125 Turin, Italy
2
Dipartimento di Chimica, University of Turin, Via P. Giuria 7, 10125 Turin, Italy
3
Regional Centre of Advanced Technologies and Materials, Department of Physical Chemistry, Faculty of Science, Palacky University, Šlechtitelů 27, 783 71 Olomouc, Czech Republic
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Molecules 2020, 25(2), 410; https://doi.org/10.3390/molecules25020410
Received: 14 December 2019 / Revised: 11 January 2020 / Accepted: 14 January 2020 / Published: 19 January 2020
(This article belongs to the Special Issue Nanocatalysis)
The optimization of sustainable protocols for reductive amination has been a lingering challenge in green synthesis. In this context, a comparative study of different metal-loaded cross-linked cyclodextrins (CDs) were examined for the microwave (MW)-assisted reductive amination of aldehydes and ketones using either H2 or formic acid as a hydrogen source. The Pd/Cu heterogeneous nanocatalyst based on Pd (II) and Cu (I) salts embedded in a β-CD network was the most efficient in terms of yield and selectivity attained. In addition, the polymeric cross-linking avoided metal leaching, thus enhancing the process sustainability; good yields were realized using benzylamine under H2. These interesting findings were then applied to the MW-assisted one-pot synthesis of secondary amines via a tandem reductive amination of benzaldehyde with nitroaromatics under H2 pressure. The formation of a CuxPdy alloy under reaction conditions was discerned, and a synergic effect due to the cooperation between Cu and Pd has been hypothesized. During the reaction, the system worked as a bifunctional nanocatalyst wherein the Pd sites facilitate the reduction of nitro compounds, while the Cu species promote the subsequent imine hydrogenation affording structurally diverse secondary amines with high yields. View Full-Text
Keywords: heterogeneous catalysis; bimetallic nanocatalyst; microwaves; one-pot reductive amination; sustainable protocols heterogeneous catalysis; bimetallic nanocatalyst; microwaves; one-pot reductive amination; sustainable protocols
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MDPI and ACS Style

Calcio Gaudino, E.; Acciardo, E.; Tabasso, S.; Manzoli, M.; Cravotto, G.; Varma, R.S. Cross-Linked Cyclodextrins Bimetallic Nanocatalysts: Applications in Microwave-Assisted Reductive Aminations. Molecules 2020, 25, 410. https://doi.org/10.3390/molecules25020410

AMA Style

Calcio Gaudino E, Acciardo E, Tabasso S, Manzoli M, Cravotto G, Varma RS. Cross-Linked Cyclodextrins Bimetallic Nanocatalysts: Applications in Microwave-Assisted Reductive Aminations. Molecules. 2020; 25(2):410. https://doi.org/10.3390/molecules25020410

Chicago/Turabian Style

Calcio Gaudino, Emanuela; Acciardo, Elisa; Tabasso, Silvia; Manzoli, Maela; Cravotto, Giancarlo; Varma, Rajender S. 2020. "Cross-Linked Cyclodextrins Bimetallic Nanocatalysts: Applications in Microwave-Assisted Reductive Aminations" Molecules 25, no. 2: 410. https://doi.org/10.3390/molecules25020410

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