ArticleJournal of the American Chemical Society2016
Iron(II)-Catalyzed Intermolecular Aminofluorination of Unfunctionalized Olefins Using Fluoride Ion.
Article in Journal of the American Chemical Society, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 33 papers.
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Who cites it
33 citing papers in PubMed.
- Advances in chemoenzymatic synthesis of glycosaminoglycans and proteoglycans.Current opinion in chemical biology · 2026Review
- Iron-catalyzed stereoselective glycosylation for 1,2-cis-aminoglycoside assembly.Nature protocols · 2026Review
- Process Safety Assessment of the Iron-Catalyzed 1,2-Organic process research & development · 2026Article
- Iron-Catalyzed Stereospecific Heterocycle N-Glycosylation with Glycal Epoxides.Organic letters · 2026Article
- Process Safety Assessment of the Iron-Catalyzed 1,2-Research square · 2026Article
- Iron-Catalyzed Stereospecific HeterocycleResearch square · 2026Article
- Merging Enzymatic Catalysis with Iron Catalysis for Highly Stereoselective Heparan Sulfate Oligosaccharide Assembly.Journal of the American Chemical Society · 2026Article
- Iron-catalyzed three-component amino(radio)fluorination of alkenes to unprotected β-(radio)fluoroamines.Nature communications · 2025Article
- Directed Evolution of Nonheme Iron Enzymes for Enantioselective Aminative Difunctionalization of Alkenes.JACS Au · 2025Article
- Biocatalytic Olefin Difunctionalization for Synthesis of Chiral 2-Azidoamines Using Nonheme Iron Enzymes.Angewandte Chemie (International ed. in English) · 2025Article
- Iron-catalysed radical difunctionalization of alkenes.Nature synthesis · 2025Article
- Iron-Catalyzed GlycalTetrahedron letters · 2025Article
- Iron-Catalyzed Stereoselective Nitrogen Atom Transfer for 1,2-Synlett : accounts and rapid communications in synthetic organic chemistry · 2025Article
- Stereoselective Multigram-Scale Tn Antigen Synthesis via the Iron-Catalyzed Glycal 1,2-Organic letters · 2025Article
- Stereoselective Glycosylation for 1,2-Journal of the American Chemical Society · 2024Article
- A Catalytic Three-Component Aminofluorination of Unactivated Alkenes with Electron-Rich Amino Sources.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Copper-Catalyzed Three-Component Aminofluorination of Alkenes and 1,3-Dienes: Direct Entry to Diverse β-Fluoroalkylamines.Journal of the American Chemical Society · 2022Article
- The advent of electrophilic hydroxylamine-derived reagents for the direct preparation of unprotected amines.Chemical communications (Cambridge, England) · 2022Review
- Regio- and Enantioselective Intermolecular Aminofluorination of Alkenes via Iodine(I)/Iodine(III) Catalysis.Angewandte Chemie (International ed. in English) · 2022Article
- Bifunctional sulfilimines enable synthesis of multiple N-heterocycles from alkenes.Nature chemistry · 2022Article
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Authors and funding
4 authors.
Funding
Abstract
We herein report a new catalytic method for intermolecular olefin aminofluorination using earth-abundant iron catalysts and nucleophilic fluoride ion. This method tolerates a broad range of unfunctionalized olefins, especially nonstyrenyl olefins that are incompatible with existing olefin aminofluorination methods. This new iron-catalyzed process directly converts readily available olefins to internal vicinal fluoro carbamates with high regioselectivity (N vs F), many of which are difficult to prepare using known methods. Preliminary mechanistic studies demonstrate that it is possible to exert asymmetric induction using chiral iron catalysts and that both an iron-nitrenoid and carbocation species may be reactive intermediates.
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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.