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

Georgia M. Richardson, Iskander Douair, Scott A. Cameron, Joe Bracegirdle, Robert A. Keyzers, Michael S. Hill (), Laurent Maron () and Mathew D. Anker ()
Additional contact information
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

Nature Communications, 2021, vol. 12, issue 1, 1-7

Abstract: 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.

Date: 2021
References: Add references at CitEc
Citations:

Downloads: (external link)
https://www.nature.com/articles/s41467-021-23444-x Abstract (text/html)

Related works:
This item may be available elsewhere in EconPapers: Search for items with the same title.

Export reference: BibTeX RIS (EndNote, ProCite, RefMan) HTML/Text

Persistent link: https://EconPapers.repec.org/RePEc:nat:natcom:v:12:y:2021:i:1:d:10.1038_s41467-021-23444-x

Ordering information: This journal article can be ordered from
https://www.nature.com/ncomms/

DOI: 10.1038/s41467-021-23444-x

Access Statistics for this article

Nature Communications is currently edited by Nathalie Le Bot, Enda Bergin and Fiona Gillespie

More articles in Nature Communications from Nature
Bibliographic data for series maintained by Sonal Shukla () and Springer Nature Abstracting and Indexing ().