ArticleOrganic letters2023
2-Fluoroenones via an Umpolung Morita-Baylis-Hillman Reaction of Enones.
Article in Organic letters, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
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Who cites it
3 citing papers in PubMed.
- Synthesis of 2,2-Disubstituted Indolin-3-ones via Enolonium Species.The Journal of organic chemistry · 2025Article
- Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents.Chemical reviews · 2024Review
- Stereospecific Conversion of Boronic Esters into Enones using Methoxyallene: Application in the Total Synthesis of 10-Deoxymethynolide.Angewandte Chemie (International ed. in English) · 2023Article
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Authors and funding
2 authors.
Funding
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Abstract
Several methods have been reported for the formation of 2-fluoroenones. However, all these methods involve laborious multiple-step sequences with resulting low overall yields. In this paper, we report the first formal enone-α-H to F substitution, leading to 2-fluoroenones in a single step from ubiquitous enones in 63-90% yield. The reaction is applicable to a wide range of aromatic and alkenyl enones and is carried out at room temperature using HF-pyridine complex as the fluoride source. Mechanistic investigations support that the reaction takes place through a rare umpolung Morita-Baylis-Hillman-type mechanism.
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