ArticleNature chemistry2019
The formation of all-cis-(multi)fluorinated piperidines by a dearomatization-hydrogenation process.
Article in Nature chemistry, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 46 papers.
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Who cites it
46 citing papers in PubMed, 148 citations in OpenAlex.
- Substrate-Controlled Dearomative Cycloadditions of Perfluoronaphthalenes via Visible-Light Energy Transfer Catalysis: Switchable Access to [2+2], [4+2], and Diastereoconvergent Cycloadducts.Angewandte Chemie (International ed. in English) · 2026Article
- Iridium(III)-catalysed ionic hydrogenation of pyridines to multisubstituted piperidines.Nature chemistry · 2026Article
- Highly selective and practical hydrogenation of functionalized (hetero)arenes.Nature communications · 2026Article
- Bioactivity Profiles of Progressively Ring-Fluorinated Cyclohexyl Motifs in the WKYMVm Peptide as Formylpeptide FPR2 Agonists and in Keto-Piperazines as Antitrypanosome Agents.Chembiochem : a European journal of chemical biology · 2025Article
- Visible-Light SThe Journal of organic chemistry · 2025Article
- Modular synthesis of bis-α-chiral amines using Ellman sulfinamide for consecutiveScience advances · 2025Article
- Origami with small molecules: exploiting the C-F bond as a conformational tool.Beilstein journal of organic chemistry · 2025Review
- Synthesis of Janus All-The Journal of organic chemistry · 2024Article
- Designing chemical systems for precision deuteration of medicinal building blocks.Nature communications · 2024Article
- Reductive Transamination of Pyridinium Salts to N-Aryl Piperidines.The Journal of organic chemistry · 2024Article
- Selective 1,4-syn-Addition to Cyclic 1,3-Dienes via Hybrid Palladium Catalysis.ACS central science · 2024Article
- Visible-Light Photocatalytic C-H Amination of Arenes Utilizing Acridine-Lewis Acid Complexes.Journal of the American Chemical Society · 2024Article
- Synthesis of polysubstituted azepanes by dearomative ring expansion of nitroarenes.Nature chemistry · 2024Article
- Late-Stage Saturation of Drug Molecules.Journal of the American Chemical Society · 2024Article
- Chemoselective Heterogeneous Hydrogenation of Sulfur Containing Quinolines under Mild Conditions.Journal of the American Chemical Society · 2024Article
- Recent Strategies in the Nucleophilic Dearomatization of Pyridines, Quinolines, and Isoquinolines.Chemical reviews · 2024Review
- Oxidative Dearomatization of Pyridines.Journal of the American Chemical Society · 2024Article
- Asymmetric arene hydrogenation: towards sustainability and application.Chemical Society reviews · 2023Review
- Chromium-catalyzed stereodivergent E- and Z-selective alkyne hydrogenation controlled by cyclic (alkyl)(amino)carbene ligands.Nature communications · 2023Article
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
Abstract
Piperidines and fluorine substituents are both independently indispensable components in pharmaceuticals, agrochemicals and materials. Logically, the incorporation of fluorine atoms into piperidine scaffolds is therefore an area of tremendous potential. However, synthetic approaches towards the formation of these architectures are often impractical. The diastereoselective synthesis of substituted monofluorinated piperidines often requires substrates with pre-defined stereochemistry. That of multifluorinated piperidines is even more challenging, and often needs to be carried out in multistep syntheses. In this report, we describe a straightforward process for the one-pot rhodium-catalysed dearomatization-hydrogenation of fluoropyridine precursors. This strategy enables the formation of a plethora of substituted all-cis-(multi)fluorinated piperidines in a highly diastereoselective fashion through pyridine dearomatization followed by complete saturation of the resulting intermediates by hydrogenation. Fluorinated piperidines with defined axial/equatorial orientation of fluorine substituents were successfully applied in the preparation of commercial drugs analogues. Additionally, fluorinated PipPhos as well as fluorinated ionic liquids were obtained by this dearomatization-hydrogenation process.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.