Alharbi, AA, Wills, C, Chamberlain, TW orcid.org/0000-0001-8100-6452 et al. (7 more authors) (2023) Amino-Modified Polymer Immobilized Ionic Liquid Stabilized Ruthenium Nanoparticles: Efficient and Selective Catalysts for the Partial and Complete Reduction of Quinolines. ChemCatChem, 15 (11). e202300418. ISSN 1867-3880
Abstract
RuNPs stabilised by amino-decorated imidazolium-based polymer immobilized ionic liquids catalyse the dimethylamine borane mediated reduction of quinolines to 1,2-dihydroquinoline (DHQ) and 1,2,3,4-tetrahydroquinoline (THQ). Partial reduction of 3-substituted quinolines to the corresponding 1,2-dihydroquinoline was achieved with 100 % selectivity in toluene under mild conditions. This is the first report of the selective partial reduction of 3-substituted quinolines to the corresponding 1,2-dihydroquinolines with a heterogeneous nanoparticle-based catalyst. A wide range of substituted quinolines have also been reduced to the corresponding 1,2,3,4-tetrahydroquinoline with high selectivity and good yields by adjusting the reaction time. The 1,2-dihydroquinolines readily release dihydrogen in toluene at 60 °C in the absence of catalyst with no evidence for disproportionation and as such are potential organo-hydride reagents. The initial TOF of 610 mol quinoline converted mol Ru−1 h−1 for the reduction of quinoline is among the highest to be reported for a metal nanoparticle-based catalyst and the conversion of 96 % obtained after 4 h at 65 °C is significantly higher than its platinum nanoparticle counterpart PtNP@NH2-PEGPIILS as well as 5 wt/% Ru/C, which only reached 9 % and 11 % conversion, respectively, at the same time. Hot filtration experiments showed that the active species was heterogeneous.
Metadata
Item Type: | Article |
---|---|
Authors/Creators: |
|
Copyright, Publisher and Additional Information: | © 2023 The Authors. This is an open access article under the terms of the Creative Commons Attribution License (CC-BY 4.0), which permits unrestricted use, distribution and reproduction in any medium, provided the original work is properly cited. |
Keywords: | supported catalysis, ruthenium nanoparticles, transfer hydrogenation, quinolines, selective partial reduction, amino-decorated polymer immobilized ionic liquids |
Dates: |
|
Institution: | The University of Leeds |
Academic Units: | The University of Leeds > Faculty of Engineering & Physical Sciences (Leeds) > School of Chemical & Process Engineering (Leeds) The University of Leeds > Faculty of Engineering & Physical Sciences (Leeds) > School of Chemistry (Leeds) > Inorganic Chemistry (Leeds) |
Depositing User: | Symplectic Publications |
Date Deposited: | 29 Jun 2023 09:16 |
Last Modified: | 29 Jun 2023 09:16 |
Status: | Published |
Publisher: | Wiley |
Identification Number: | 10.1002/cctc.202300418 |
Related URLs: | |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:200643 |