Open Access Te Herenga Waka-Victoria University of Wellington
Browse

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

journal contribution
posted on 2021-06-09, 04:59 authored by GM Richardson, I Douair, Scott CameronScott Cameron, Joe Bracegirdle, Robert KeyzersRobert Keyzers, MS Hill, L Maron, Mathew AnkerMathew Anker
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, [BDI YbH] (BDI = CH[C(CH )NDipp] , Dipp = 2,6-diisopropylphenyl), reacts with ethene and propene to provide the ytterbium(II) n-alkyls, [BDI YbR] (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 (S 2) displacement of hydride, while the resultant regeneration of [BDI YbH] facilitates further reaction with ethene or propene and enables the direct catalytic (anti-Markovnikov) hydroarylation of both alkenes with a benzene C-H bond. Dipp Dipp Dipp Dipp 2 3 2 2 N 2

History

Preferred citation

Richardson, G. M., Douair, I., Cameron, S. A., Bracegirdle, J., Keyzers, R. A., Hill, M. S., Maron, L. & Anker, M. D. (2021). Hydroarylation of olefins catalysed by a dimeric ytterbium(II) alkyl. Nature Communications, 12(1), 3147-. https://doi.org/10.1038/s41467-021-23444-x

Journal title

Nature Communications

Volume

12

Issue

1

Publication date

2021-12-01

Pagination

3147

Publisher

Springer Science and Business Media LLC

Publication status

Accepted

Online publication date

2021-05-25

ISSN

2041-1723

eISSN

2041-1723

Article number

3147

Language

en

Usage metrics

    Journal articles

    Categories

    No categories selected

    Licence

    Exports

    RefWorks
    BibTeX
    Ref. manager
    Endnote
    DataCite
    NLM
    DC