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Hydroarylation of olefins catalysed by a dimeric ytterbium(II) alkyl

Author

Listed:
  • Georgia M. Richardson

    (School of Chemical and Physical Sciences, Victoria University of Wellington)

  • Iskander Douair

    (Université de Toulouse et CNRS, INSA, UPS, UMR 5215)

  • Scott A. Cameron

    (Ferrier Research Institute, Victoria University of Wellington)

  • Joe Bracegirdle

    (School of Chemical and Physical Sciences, Victoria University of Wellington)

  • Robert A. Keyzers

    (School of Chemical and Physical Sciences, Victoria University of Wellington)

  • Michael S. Hill

    (University of Bath)

  • Laurent Maron

    (Université de Toulouse et CNRS, INSA, UPS, UMR 5215)

  • Mathew D. Anker

    (School of Chemical and Physical Sciences, Victoria University of Wellington)

Abstract

Although the nucleophilic alkylation of aromatics has recently been achieved with a variety of potent main group reagents, all of this reactivity is limited to a stoichiometric regime. We now report that the ytterbium(II) hydride, [BDIDippYbH]2 (BDIDipp = CH[C(CH3)NDipp]2, Dipp = 2,6-diisopropylphenyl), reacts with ethene and propene to provide the ytterbium(II) n-alkyls, [BDIDippYbR]2 (R = Et or Pr), both of which alkylate benzene at room temperature. Density functional theory (DFT) calculations indicate that this latter process operates through the nucleophilic (SN2) displacement of hydride, while the resultant regeneration of [BDIDippYbH]2 facilitates further reaction with ethene or propene and enables the direct catalytic (anti-Markovnikov) hydroarylation of both alkenes with a benzene C-H bond.

Suggested Citation

  • Georgia M. Richardson & Iskander Douair & Scott A. Cameron & Joe Bracegirdle & Robert A. Keyzers & Michael S. Hill & Laurent Maron & Mathew D. Anker, 2021. "Hydroarylation of olefins catalysed by a dimeric ytterbium(II) alkyl," Nature Communications, Nature, vol. 12(1), pages 1-7, December.
    • Handle: RePEc:nat:natcom:v:12:y:2021:i:1:d:10.1038_s41467-021-23444-x
    DOI: 10.1038/s41467-021-23444-x
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