ArticleJournal of the American Chemical Society2016
Ru-Catalyzed C-H Arylation of Fluoroarenes with Aryl Halides.
Article in Journal of the American Chemical Society, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.
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Who cites it
21 citing papers in PubMed.
- Arene Ruthenium(II) Carboxylates for C─H Alkylations and Arylations at Near Room Temperature.Angewandte Chemie (International ed. in English) · 2025Article
- An air- and moisture-stable ruthenium precatalyst for diverse reactivity.Nature chemistry · 2024Article
- Applications of Transition Metal-CatalyzedChemical reviews · 2024Review
- Protodemetalation of (Bipyridyl)Ni(II)-Aryl Complexes Shows Evidence for Five-, Six-, and Seven-Membered Cyclic Pathways.Journal of the American Chemical Society · 2023Article
- DFT Case Study on the Comparison of Ruthenium-Catalyzed C-H Allylation, C-H Alkenylation, and Hydroarylation.ACS omega · 2022Article
- Photo-Induced Ruthenium-Catalyzed C-H Benzylations and Allylations at Room Temperature.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Stereoselective rhodium-catalyzed 2-C-H 1,3-dienylation of indoles: dual functions of the directing group.Chemical science · 2021Article
- Transition-Metal-Free Coupling of Polyfluorinated Arenes and Functionalized, Masked Aryl Nucleophiles.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Direct Arylation in the Presence of Palladium Pincer Complexes.Molecules (Basel, Switzerland) · 2021Review
- Decarboxylative Polyfluoroarylation of Alkylcarboxylic Acids.Angewandte Chemie (International ed. in English) · 2021Article
- The site-selectivity and mechanism of Pd-catalyzed C(spChemical science · 2020Article
- Photo-Induced Ruthenium-Catalyzed C-H Arylations at Ambient Temperature.Angewandte Chemie (International ed. in English) · 2020Article
- Article
- C-H Oxygenation Reactions Enabled by Dual Catalysis with Electrogenerated Hypervalent Iodine Species and Ruthenium Complexes.Angewandte Chemie (International ed. in English) · 2020Article
- Ag/Pd Cocatalyzed Direct Arylation of Fluoroarene Derivatives with Aryl Bromides.ACS catalysis · 2020Article
- Oligothiophene Synthesis by a General C-H Activation Mechanism:ACS catalysis · 2019Article
- Benzoate Cyclometalation Enables Oxidative Addition of Haloarenes at a Ru(II) Center.Journal of the American Chemical Society · 2018Article
- Cyclometallated ruthenium catalyst enables late-stage directed arylation of pharmaceuticals.Nature chemistry · 2018Article
- Highly chemoselective ruthenium(ii)-catalyzed direct arylation of cyclic andChemical science · 2017Article
- Ruthenium-Catalyzed C-H Arylation of Benzoic Acids and Indole Carboxylic Acids with Aryl Halides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2017Article
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Authors and funding
6 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Although the ruthenium-catalyzed C-H arylation of arenes bearing directing groups with haloarenes is well-known, this process has never been achieved in the absence of directing groups. We report the first example of such a process and show that unexpectedly the reaction only takes place in the presence of catalytic amounts of a benzoic acid. Furthermore, contrary to other transition metals, the arylation site selectivity is governed by both electronic and steric factors. Stoichiometric and NMR mechanistic studies support a catalytic cycle that involves a well-defined η(6)-arene-ligand-free Ru(II) catalyst. Indeed, upon initial pivalate-assisted C-H activation, the aryl-Ru(II) intermediate generated is able to react with an aryl bromide coupling partner only in the presence of a benzoate additive. In contrast, directing-group-containing substrates (such as 2-phenylpyridine) do not require a benzoate additive. Deuterium labeling and kinetic isotope effect experiments indicate that C-H activation is both reversible and kinetically significant. Computational studies support a concerted metalation-deprotonation (CMD)-type ruthenation mode and shed light on the unusual arylation regioselectivity.
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