ArticleJournal of the American Chemical Society2018
Benzoate Cyclometalation Enables Oxidative Addition of Haloarenes at a Ru(II) Center.
Article in Journal of the American Chemical Society, 2018. 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.
- The Mechanism of Ruthenium-Catalyzed Directed C─H Arylation of Arenes: The Key Role of Bis-Cyclometalated Intermediates.Angewandte Chemie (International ed. in English) · 2025Article
- Photo-Induced Ruthenium-Catalyzed C-H Benzylations and Allylations at Room Temperature.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Photo-Induced Ruthenium-Catalyzed C-H Arylations at Ambient Temperature.Angewandte Chemie (International ed. in English) · 2020Article
- Cyclometalated Ruthenium Pincer Complexes as Catalysts for the α-Alkylation of Ketones with Alcohols.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Cross-Coupling and Related Reactions: Connecting Past Success to the Development of New Reactions for the Future.Organometallics · 2019Article
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Authors and funding
4 authors.
Funding
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Abstract
The first Ru(II)-catalyzed arylation of substrates without a directing group was recently developed. Remarkably, this process only worked in the presence of a benzoate additive, found to be crucial for the oxidative addition step at Ru(II). However, the exact mode of action of the benzoate was unknown. Herein, we disclose a mechanistic study that elucidates the key role of the benzoate salt in the C-H arylation of fluoroarenes with aryl halides. Through a combination of rationally designed stoichiometric experiments and DFT studies, we demonstrate that the aryl-Ru(II) species arising from initial C-H activation of the fluoroarene undergoes cyclometalation with the benzoate to generate an anionic Ru(II) intermediate. The enhanced lability of this intermediate, coupled with the electron-rich anionic Ru(II) metal center renders the oxidative addition of the aryl halide accessible. The role of an additional (NMe
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