ArticleJournal of the American Chemical Society2024
Dialumene as a Dimeric or Monomeric Al Synthon for C-F Activation in Monofluorobenzene.
Article in Journal of the American Chemical Society, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- Speciation-Controlled C-F Bond Functionalization Enabled by Zwitterionic Pnictinidenes.Angewandte Chemie (International ed. in English) · 2026Article
- Aluminylation: a generalizable route towards low-valent aluminum under moderate conditions with controlled product nuclearity through precursor design.Chemical science · 2026Article
- Why is a dicationic digallene so reactive towards activation of strong covalent bonds? Scope and mechanistic investigations.Chemical science · 2026Article
- Isolable radical cation and dication of dialumene.Nature communications · 2026Article
- Cryogenic Organometallic Carbon-Fluoride Bond Functionalization with Broad Functional Group Tolerance.Journal of the American Chemical Society · 2025Article
Corrections and comments
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Authors and funding
4 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The activation of C-F bonds has long been regarded as the subject of research in organometallic chemistry, given their synthetic relevance and the fact that fluorine is the most abundant halogen in the Earth's crust. However, C-F bond activation remains a largely unsolved challenge due to the high bond dissociation energies, which was historically dominated by transition metal complexes. Main group elements that can cleave unactivated monofluorobenzene are still quite rare and restricted to s-block complexes with a biphilic nature. Herein, we demonstrate an Al-mediated activation of monofluorobenzene using a neutral dialumene, allowing for the synthesis of the formal oxidative addition products at either double or single aluminum centers. This neutral dialumene system introduces a novel methodology for C-F bond activation based on formal oxidative addition and reductive elimination processes around the two aluminum centers, as demonstrated by combined experimental and computational studies. A "masked" alumylene was unprecedentedly synthesized to prove the proposed reductive elimination pathway. Furthermore, the synthetic utility is highlighted by the functionalization of the resulting aryl-aluminum compounds.
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Registered trials
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