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Heteroatom Donor-Decorated Polymer-Immobilized Ionic Liquid Stabilized Palladium Nanoparticles: Efficient Catalysts for Room-Temperature Suzuki-Miyaura Cross-Coupling in Aqueous Media

Lookup NU author(s): Dr Simon Doherty, Dr Julian Knight, Tom Backhouse, Einas Abood, Hind Alshaikh, Ashley Clemmet, Jack Ellison

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This is the authors' accepted manuscript of an article that has been published in its final definitive form by Wiley - VCH Verlag GmbH & Co. KGaA, 2018.

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Abstract

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 condtions. 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 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. Keywords: Palladium nanoparticles; immobilised ionic liquids; heteroatom donor; stabilisation; Suzuki cross coupling; aqueous media


Publication metadata

Author(s): Doherty S, Knight JG, Backhouse T, Abood E, Alshaikh H, Clemmet AR, Ellison JR, Bourne RA, Chamberlain TW, Stones R, Warren NJ, Fairlamb IAJ, Lovelock KRJ

Publication type: Article

Publication status: Published

Journal: Advanced Synthesis & Catalysis

Year: 2018

Volume: 360

Issue: 19

Pages: 3716-3731

Print publication date: 04/10/2018

Online publication date: 17/07/2018

Acceptance date: 07/06/2018

Date deposited: 17/07/2018

ISSN (print): 1615-4150

ISSN (electronic): 1615-4169

Publisher: Wiley - VCH Verlag GmbH & Co. KGaA

URL: https://doi.org/10.1002/adsc.201800561

DOI: 10.1002/adsc.201800561


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