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


Publication details

JournalAdvanced Synthesis and Catalysis
DateAccepted/In press - 12 Jul 2018
DateE-pub ahead of print - 3 Aug 2018
DatePublished (current) - 4 Oct 2018
Number of pages17
Pages (from-to)1-17
Early online date3/08/18
Original languageEnglish


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.

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© 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

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