ArticleBeilstein journal of organic chemistry2018
Cross-coupling of dissimilar ketone enolates via enolonium species to afford non-symmetrical 1,4-diketones.
Article in Beilstein journal of organic chemistry, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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13 citing papers in PubMed.
- Cationic, Iodine(III)-Mediated and Directed Diastereoselective Oxidation of Inert C-H Bonds in Cyclic Hydrocarbons.Angewandte Chemie (International ed. in English) · 2025Article
- Stereoselective Synthesis of 1,n-Dicarbonyl Compounds Through Palladium-Catalyzed Ring Opening/Isomerization of Densely Substituted Cyclopropanols.Angewandte Chemie (International ed. in English) · 2025Article
- Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents.Chemical reviews · 2024Review
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- Article
- 2-Fluoroenones via an Umpolung Morita-Baylis-Hillman Reaction of Enones.Organic letters · 2023Article
- Silver-Catalyzed Controlled Intermolecular Cross-Coupling of Silyl Enol Ethers: Scalable Access to 1,4-Diketones.Organic letters · 2022Article
- Sulfur(iv)-mediated umpolung α-heterofunctionalization of 2-oxazolines.Chemical science · 2022Article
- Recent discoveries on the structure of iodine(iii) reagents and their use in cross-nucleophile coupling.Chemical science · 2021Review
- An α-Cyclopropanation of Carbonyl Derivatives by Oxidative Umpolung.Angewandte Chemie (International ed. in English) · 2020Article
- Direct C-H α-Arylation of Enones with ArI(OJournal of the American Chemical Society · 2020Article
- Stereoselective synthesis of alkyl-, aryl-, vinyl- and alkynyl-substitutedChemical science · 2019Article
- A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species.Journal of visualized experiments : JoVE · 2018Article
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4 authors.
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Abstract
Due to their closely matched reactivity, the coupling of two dissimilar ketone enolates to form a 1,4-diketone remains a challenge in organic synthesis. We herein report that umpolung of a ketone trimethylsilyl enol ether (1 equiv) to form a discrete enolonium species, followed by addition of as little as 1.2-1.4 equivalents of a second trimethylsilyl enol ether, provides an attractive solution to this problem. A wide array of enolates may be used to form the 1,4-diketone products in 38 to 74% yield. Due to the use of two TMS enol ethers as precursors, an optimization of the cross-coupling should include investigating the order of addition.
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