ArticleJournal of the American Chemical Society2019
Catalytic Carbonyl-Olefin Metathesis of Aliphatic Ketones: Iron(III) Homo-Dimers as Lewis Acidic Superelectrophiles.
Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 23 papers.
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Who cites it
23 citing papers in PubMed.
- Carbonyl-Olefin/Alkyne Metathesis Reactions Catalyzed by Bifunctional H-USY Zeolites.Journal of the American Chemical Society · 2025Article
- Intermolecular SpAngewandte Chemie (International ed. in English) · 2025Article
- Theoretical Investigations of Substrate Behavior in FeClACS omega · 2025Article
- Cyclization Strategies in Carbonyl-Olefin Metathesis: An Up-to-Date Review.Molecules (Basel, Switzerland) · 2024Review
- Highlights from the 57th Bürgenstock Conference on Stereochemistry 2024.Chemical science · 2024Article
- Iron-Mediated Photochemical Anti-Markovnikov Hydroazidation of Unactivated Olefins.Journal of the American Chemical Society · 2023Article
- Controlling Catalyst Behavior in Lewis Acid-Catalyzed Carbonyl-Olefin Metathesis.Journal of the American Chemical Society · 2023Article
- Olefination of carbonyls with alkenes enabled by electrophotocatalytic generation of distonic radical cations.Science advances · 2023Article
- Article
- Hydrazone and Oxime Olefination via Ruthenium Alkylidenes.Angewandte Chemie (International ed. in English) · 2022Article
- Synergistic Brønsted/Lewis acid catalyzed aromatic alkylation with unactivated tertiary alcohols or di-Chemical science · 2022Article
- Hydrogen Bonding Networks Enable Brønsted Acid-Catalyzed Carbonyl-Olefin Metathesis.Angewandte Chemie (International ed. in English) · 2022Article
- Carbonyl-Olefin Metathesis.Chemical reviews · 2021Review
- Combined Theoretical and Experimental Investigation of Lewis Acid-Carbonyl Interactions for Metathesis.ACS catalysis · 2021Article
- Brønsted-Acid-Catalyzed Intramolecular Carbonyl-Olefin Reactions: Interrupted Metathesis vs Carbonyl-Ene Reaction.The Journal of organic chemistry · 2021Article
- Superelectrophiles: Recent Advances.Molecules (Basel, Switzerland) · 2020Review
- Ring-opening carbonyl-olefin metathesis of norbornenes.Chemical science · 2020Article
- Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy.Journal of visualized experiments : JoVE · 2020Article
- Investigation of Lewis Acid-Carbonyl Solution Interactions via Infrared-Monitored Titration.The Journal of organic chemistry · 2020Article
- Catalytic, transannular carbonyl-olefin metathesis reactions.Chemical science · 2019Article
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9 authors.
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Abstract
Catalytic carbonyl-olefin metathesis reactions have recently been developed as a powerful tool for carbon-carbon bond formation. However, currently available synthetic protocols rely exclusively on aryl ketone substrates while the corresponding aliphatic analogs remain elusive. We herein report the development of Lewis acid-catalyzed carbonyl-olefin ring-closing metathesis reactions for aliphatic ketones. Mechanistic investigations are consistent with a distinct mode of activation relying on the in situ formation of a homobimetallic singly bridged iron(III)-dimer as the postulated active catalytic species. These "superelectrophiles" function as more powerful Lewis acid catalysts that form upon association of individual iron(III)-monomers. While this mode of Lewis acid activation has previously been postulated to exist, it has not yet been applied in a catalytic setting. The insights presented are expected to enable further advancement in Lewis acid catalysis by building upon the activation principle of "superelectrophiles" and to broaden the current scope of catalytic carbonyl-olefin metathesis reactions.
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