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

Georgia Richardson, Iskander Douair, Scott Cameron, Joe Bracegirdle, Robert Keyzers, Michael Hill, Laurent Maron, Mathew Anker

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10 Citations (SciVal)


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.
Original languageEnglish
Article number3147
Number of pages7
JournalNature Communications
Issue number1
Publication statusPublished - 25 May 2021

ASJC Scopus subject areas

  • Physics and Astronomy(all)
  • Chemistry(all)
  • Biochemistry, Genetics and Molecular Biology(all)


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