ArticleNature chemistry2021
Orthogonal cross-coupling through intermolecular metathesis of unstrained C(aryl)-C(aryl) single bonds.
Article in Nature chemistry, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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12 citing papers in PubMed, 31 citations in OpenAlex.
- Catalytic C-Demethylation of Phenols and Anilines Enabled by a Removable Mono-Directing Group.Journal of the American Chemical Society · 2026Article
- Direct metathesis of carbon-carbonChemical science · 2026Article
- Nickel-Catalyzed Aryl Group Interconversion: A Non-Equilibrium Strategy for Aryl Nitrile Synthesis.JACS Au · 2026Article
- Heteroaromatic swapping in aromatic ketones.Nature communications · 2025Article
- Skeletal Modification via Activation of Relatively Unstrained C-C Bonds.Accounts of chemical research · 2025Article
- Intermolecular C-C/C-N σ-bond metathesis enabled by visible light.Chemical science · 2024Article
- Split cross-coupling via Rh-catalysed activation of unstrained aryl-aryl bonds.Nature catalysis · 2024Article
- Diazene-Catalyzed Oxidative Alkyl Halide-Olefin Metathesis.Organic letters · 2024Article
- Nickel-catalyzed skeletal transformation of tropone derivativesChemical science · 2022Article
- Catalytic Activation of Unstrained C(Aryl)-C(Alkyl) Bonds in 2,2'-Methylenediphenols.Journal of the American Chemical Society · 2022Article
- Carbon-carbon bond activation by B(OMe)Chemical science · 2021Article
- Mastering mono-bond metathesis.Nature chemistry · 2021Article
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3 authors at 2 institutions in 1 country.
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Abstract
While metathesis reactions involving carbon-carbon double bonds, namely olefin metathesis, have been well established with broad utility in organic synthesis and materials science, direct metathesis of kinetically less accessible C-C single bonds is extremely rare. Here we report a ruthenium-catalysed reversible C-C single-bond metathesis reaction that allows redox- and pH-neutral biaryl synthesis. Assisted by directing groups, unstrained homo-biaryl compounds undergo aryl exchanges to generate cross-biaryl products, catalysed by a well-defined air-stable ruthenium(II) complex. Functional groups reactive under typical cross-coupling reactions, such as halogen, silyl and boronate moieties, are compatible under the metathesis conditions. Mechanistic studies disclose an intriguing 'olefin-metathesis-like' pathway that involves an unexpected heptacoordinated, 18-electron closed-shell intermediate. The distinct reaction mode discovered here is expected to inspire the development of more general C-C single-bond metathesis and orthogonal cross-coupling reactions.
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