Doherty, S, Knight, JG, Backhouse, T et al. (10 more authors) (2018) Heteroatom Donor‐Decorated Polymer‐Immobilized Ionic Liquid Stabilized Palladium Nanoparticles: Efficient Catalysts for Room‐Temperature Suzuki‐Miyaura Cross‐Coupling in Aqueous Media. Advanced Synthesis and Catalysis, 360 (19). pp. 3716-3731. ISSN 1615-4150
Abstract
Palladium nanoparticles stabilized by heteroatom donor‐modified polystyrene‐based polymer immobilized ionic liquids (PdNP@HAD‐PIILP; HAD‐PPh₂, OMe, NH₂, CN, pyrrolidone) are highly efficient catalysts for the Suzuki‐Miyaura cross‐coupling in aqueous media under mild conditions. Catalyst modified with phosphine was consistently the most efficient as it gave high yields across a range of substrates under mild conditions at low catalyst loadings. Incorporation of polyethylene glycol into the phosphine modified immobilised ionic liquid support improved catalyst efficacy by improving dispersibility and facilitating access to the active site. Moreover, each of the heteroatom modified catalysts was more active than the corresponding unsubstituted imidazolium‐based polystyrene benchmark as well as commercial samples of Pd/C. Catalyst generated in situ from either [PdCl₄]@PPh₂‐PIILP or its PEGylated counterpart [PdCl₄]@PPh₂‐PEGPIILP, by reduction with phenylboronic acid, outperformed their pre‐formed counterparts for the vast majority of substrates examined. The turnover frequency of 16,300 h⁻¹ obtained at room temperature is one of the highest to be reported for palladium nanoparticle‐catalysed Suzuki‐Miyaura cross‐coupling between 4‐bromoacetophenone and phenylboronic acid in aqueous media under such mild conditions.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim. This is the peer reviewed version of the following article: Doherty, S. , Knight, J. G., Backhouse, T. , Abood, E. , Al‐shaikh, H. , Clemmet, A. R., Ellison, J. R., Bourne, R. A., Chamberlain, T. W., Stones, R. , Warren, N. J., Fairlamb, I. A. and Lovelock, K. R. (2018), Heteroatom Donor‐Decorated Polymer‐Immobilized Ionic Liquid Stabilized Palladium Nanoparticles: Efficient Catalysts for Room‐Temperature Suzuki‐Miyaura Cross‐Coupling in Aqueous Media. Adv. Synth. Catal., which has been published in final form at https://doi.org/10.1002/adsc.201800561. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving. Uploaded in accordance with the publisher's self-archiving policy. |
Keywords: | Palladium nanoparticles; immobilised ionic liquids; heteroatom donor; stabilisation; Suzuki-Miyaura cross-coupling; aqueous media |
Dates: |
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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: | 19 Jul 2018 11:58 |
Last Modified: | 17 Jul 2019 00:39 |
Status: | Published |
Publisher: | Wiley |
Identification Number: | 10.1002/adsc.201800561 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:133470 |