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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

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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. / Doherty, Simon; Knight, Julian; Backhouse, Tom; Abood, Einas; Alshaikh, Hind; Clement, Ashley; Ellison, Jack; Bourne, Richard; Chamberlain, Thomas ; Stones, Rebecca; Warren, Nicholas; Fairlamb, Ian James Stewart; Lovelock, Kevin .

In: Advanced Synthesis and Catalysis, 04.10.2018, p. 1-17.

Research output: Contribution to journalArticle

Harvard

Doherty, S, Knight, J, Backhouse, T, Abood, E, Alshaikh, H, Clement, A, Ellison, J, Bourne, R, Chamberlain, T, Stones, R, Warren, N, Fairlamb, IJS & Lovelock, K 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, pp. 1-17. https://doi.org/10.1002/adsc.201800561

APA

Doherty, S., Knight, J., Backhouse, T., Abood, E., Alshaikh, H., Clement, A., ... Lovelock, K. (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, 1-17. https://doi.org/10.1002/adsc.201800561

Vancouver

Doherty S, Knight J, Backhouse T, Abood E, Alshaikh H, Clement A et al. 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. 2018 Oct 4;1-17. https://doi.org/10.1002/adsc.201800561

Author

Doherty, Simon ; Knight, Julian ; Backhouse, Tom ; Abood, Einas ; Alshaikh, Hind ; Clement, Ashley ; Ellison, Jack ; Bourne, Richard ; Chamberlain, Thomas ; Stones, Rebecca ; Warren, Nicholas ; Fairlamb, Ian James Stewart ; Lovelock, Kevin . / Heteroatom Donor‐Decorated Polymer‐Immobilized Ionic Liquid Stabilized Palladium Nanoparticles : Efficient Catalysts for Room‐Temperature Suzuki‐Miyaura Cross‐Coupling in Aqueous Media. In: Advanced Synthesis and Catalysis. 2018 ; pp. 1-17.

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@article{304ef1f4cecf47d7a0715755b4b3192c,
title = "Heteroatom Donor‐Decorated Polymer‐Immobilized Ionic Liquid Stabilized Palladium Nanoparticles: Efficient Catalysts for Room‐Temperature Suzuki‐Miyaura Cross‐Coupling in Aqueous Media",
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.",
author = "Simon Doherty and Julian Knight and Tom Backhouse and Einas Abood and Hind Alshaikh and Ashley Clement and Jack Ellison and Richard Bourne and Thomas Chamberlain and Rebecca Stones and Nicholas Warren and Fairlamb, {Ian James Stewart} and Kevin Lovelock",
note = "{\circledC} John Wiley, 2018. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details",
year = "2018",
month = "10",
day = "4",
doi = "10.1002/adsc.201800561",
language = "English",
pages = "1--17",
journal = "Advanced Synthesis and Catalysis",
issn = "1615-4150",
publisher = "Wiley-VCH Verlag",

}

RIS (suitable for import to EndNote) - Download

TY - JOUR

T1 - Heteroatom Donor‐Decorated Polymer‐Immobilized Ionic Liquid Stabilized Palladium Nanoparticles

T2 - Efficient Catalysts for Room‐Temperature Suzuki‐Miyaura Cross‐Coupling in Aqueous Media

AU - Doherty, Simon

AU - Knight, Julian

AU - Backhouse, Tom

AU - Abood, Einas

AU - Alshaikh, Hind

AU - Clement, Ashley

AU - Ellison, Jack

AU - Bourne, Richard

AU - Chamberlain, Thomas

AU - Stones, Rebecca

AU - Warren, Nicholas

AU - Fairlamb, Ian James Stewart

AU - Lovelock, Kevin

N1 - © John Wiley, 2018. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details

PY - 2018/10/4

Y1 - 2018/10/4

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=85048359856&partnerID=8YFLogxK

U2 - 10.1002/adsc.201800561

DO - 10.1002/adsc.201800561

M3 - Article

SP - 1

EP - 17

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

SN - 1615-4150

ER -