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Amino-Modified Polymer Immobilized Ionic Liquid Stabilized Ruthenium Nanoparticles: Efficient and Selective Catalysts for the Partial and Complete Reduction of Quinolines

Lookup NU author(s): Dr Simon DohertyORCiD, Dr Julian Knight, Adhwa Alharbi, Dr Corinne Wills

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This work is licensed under a Creative Commons Attribution 4.0 International License (CC BY 4.0).

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 ºC 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.

Publication metadata

Author(s): Doherty S, Knight JG, Alharbi AA, Wills C, Chamberlain TW, Bourne RA, Griffiths A, Collins SM, Wu K, Mueller P

Publication type: Article

Publication status: Published

Journal: ChemCatChem

Year: 2023

Volume: 15

Issue: 11

Print publication date: 09/06/2023

Online publication date: 13/04/2023

Acceptance date: 12/04/2023

Date deposited: 13/04/2023

ISSN (electronic): 1867-3899

Publisher: Wiley-VCH Verlag GmbH & Co. KGaA

URL: https://doi.org/10.1002/cctc.202300418

DOI: 10.1002/cctc.202300418

Data Access Statement: The data that support the findings of this study are available in the supplementary material of this article.

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