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

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

Research output: Contribution to journalArticlepeer-review

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.
Original languageEnglish
Article number3147
Number of pages7
JournalNature Communications
Volume12
DOIs
Publication statusPublished - 25 May 2021

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