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

journal contribution
posted on 09.06.2021, 04:59 by GM Richardson, I Douair, Scott CameronScott Cameron, Joe BracegirdleJoe 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

01/12/2021

Pagination

3147

Publisher

Springer Science and Business Media LLC

Publication status

Accepted

Online publication date

25/05/2021

ISSN

2041-1723

eISSN

2041-1723

Article number

3147

Language

en

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