C‐N Bond Formation Catalyzed by Ruthenium Nanoparticles Supported on N‐Doped Carbon via Acceptorless Dehydrogenation to Secondary Amines, Imines, Benzimidazoles and Quinoxalines

Bin Guo; Hong-Xi Li; Shi-Qi Zhang; David James Young; Jian-Ping Lang

doi:10.1002/cctc.201801525

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C‐N Bond Formation Catalyzed by Ruthenium Nanoparticles Supported on N‐Doped Carbon via Acceptorless Dehydrogenation to Secondary Amines, Imines, Benzimidazoles and Quinoxalines

Journal article

Open access

Peer reviewed

C‐N Bond Formation Catalyzed by Ruthenium Nanoparticles Supported on N‐Doped Carbon via Acceptorless Dehydrogenation to Secondary Amines, Imines, Benzimidazoles and Quinoxalines

Bin Guo, Hong-Xi Li, Shi-Qi Zhang, David James Young and Jian-Ping Lang

ChemCatChem, Vol.10(24), pp.5627-5636

2018

DOI: https://doi.org/10.1002/cctc.201801525

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C‐N Bond Formation Catalyzed by Ruthenium Nanoparticles Supported on N‐Doped Carbon via Acceptorless Dehydrogenation to Secondary Amines, Imines, Benzimidazoles and Quinoxalines3.45 MBDownload View

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Abstract

ADC reaction

ATH reaction

recyclability

ruthenium nanoparticles

selectivity

Ruthenium nanoparticles (NPs) supported on N-doped carbon (Ru/N-C) were prepared by the pyrolysis of cis-Ru(phen)2Cl2 loaded onto carbon powder (VULCAN XC72R) at 800 ºC. Ru/N-C NPs (0.2 mol% Ru) selectively catalyzed either acceptorless dehydrogenation coupling (ADC) or auto-transfer-hydrogen (ATH) reactions of amines with alcohols to imines and secondary amines. Such selectivity could be controlled by the choice of alkali metal ion associated with the base. Under similar catalytic conditions, the ADC cross-coupling of diamines with primary alcohols or diols afforded the corresponding benzimidazoles and quinoxalines in good to excellent yields. This catalytic system displayed good activity, recyclability, and wide applicability to a diverse range of substrates.

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Title: C‐N Bond Formation Catalyzed by Ruthenium Nanoparticles Supported on N‐Doped Carbon via Acceptorless Dehydrogenation to Secondary Amines, Imines, Benzimidazoles and Quinoxalines
Authors: Bin Guo (Author) - Soochow University
Hong-Xi Li (Corresponding Author) - Soochow University
Shi-Qi Zhang (Author) - Soochow University
David James Young (Author) - University of the Sunshine Coast, Queensland, Faculty of Science, Health, Education and Engineering
Jian-Ping Lang (Corresponding Author) - Soochow University
Publication details: ChemCatChem, Vol.10(24), pp.5627-5636
Publisher: Wiley - V C H Verlag GmbH & Co. KGaA
Date published: 2018
DOI: 10.1002/cctc.201801525
ISSN: 1867-3880
Copyright note: Copyright (c) 2018. This is the peer reviewed version of the following article: B. Guo, H.-X. Li, S.-Q. Zhang, D. J. Young, J.-P. Lang, ChemCatChem 2018, 10, 5627., which has been published in final form at https://doi.org/10.1002/cctc.201801525. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.
Organisation Unit: University of the Sunshine Coast, Queensland
Language: English
Record Identifier: 99450866202621
Output Type: Journal article

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Collaboration types: Domestic collaboration; International collaboration
Web Of Science research areas: Chemistry, Physical