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

• DOI: 10.1002/adsc.201800561
• Publication Date: 2018-07-19T00:06:31Z
• Authors: Simon Doherty; Julian G. Knight; Tom Backhouse; Einas Abood; Hind Al‐shaikh; Ashley R. Clemmet; Jack R. Ellison; Richard A. Bourne; Thomas W. Chamber...; Rebecca Stones; Nicholas J. Warren; Ian J. S. Fairlamb; Kevin R. J. Lovelock
• Keywords: Phenylboronic acid; Heteroatom; Polystyrene; Coupling reaction; Suzuki reaction

Abstract Palladium nanoparticles stabilized by heteroatom donor‐modified polystyrene‐based polymer immobilized ionic liquids (PdNP@HAD‐PIILP; HAD‐PPh 2 , OMe, NH CN, pyrrolidone) are highly efficient catalysts for the Suzuki‐Miyaura cross‐coupling in aqueous media under mild conditions. Catalyst modified with phosphine was consistently most as it gave high yields across a range of substrates conditions at low catalyst loadings. Incorporation polyethylene glycol into immobilised liquid support improved efficacy improving dispersibility and facilitating access to active site. Moreover, each more than corresponding unsubstituted imidazolium‐based polystyrene benchmark well commercial samples Pd/C. generated situ from either [PdCl 4 ]@PPh ‐PIILP or its PEGylated counterpart ‐PEGPIILP, reduction phenylboronic acid, outperformed their pre‐formed counterparts vast majority examined. The turnover frequency 16,300 h −1 obtained room temperature is one highest be reported palladium nanoparticle‐catalysed between 4‐bromoacetophenone acid such magnified image