ArticleJournal of the American Chemical Society2021
Generation of Axially Chiral Fluoroallenes through a Copper-Catalyzed Enantioselective β-Fluoride Elimination.
Article in Journal of the American Chemical Society, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed.
- Expedient synthesis of poly-aryl substituted allenylsilanesRSC advances · 2026Article
- Electrochemical synthesis of allenyl silanes and allenyl boronic esters.Nature communications · 2025Article
- Capturing Unstable Carbanionic Intermediates via Halogen Transfer: Base-Promoted Oxidative Coupling Reactions of α,α-Difluoromethylarenes.Angewandte Chemie (International ed. in English) · 2025Article
- Characterization of the Active Enantiomer and Mapping of the Stereospecific Intermolecular Pattern of a Reference P2X7 Allosteric Antagonist.ACS pharmacology & translational science · 2025Article
- Copper-catalyzed highly switchable defluoroborylation and hydrodefluorination of 1-(trifluoromethyl)alkynes.Nature communications · 2024Article
- Chemo-, regio-, and stereoselective tetrafunctionalization of fluoroalkynes enables divergent synthesis of 5-7-membered azacycles.Chemical science · 2024Article
- Enantioselective and Regiodivergent Synthesis of Propargyl- and Allenylsilanes through Catalytic Propargylic C-H Deprotonation.Angewandte Chemie (International ed. in English) · 2024Article
- A review of frustrated Lewis pair enabled monoselective C-F bond activation.Chemical science · 2024Review
- Synthetic Advantages of Defluorinative C-F Bond Functionalization.Angewandte Chemie (International ed. in English) · 2023Review
- Nickel-catalysed asymmetric hydromonofluoromethylation of 1,3-enynes for enantioselective construction of monofluoromethyl-tethered chiral allenes.Chemical science · 2023Article
- A Pd-catalyzed highly selective three-component protocol for trisubstituted allenes.Chemical science · 2023Article
- Ferrocene derivatives with planar chirality and their enantioseparation by liquid-phase techniques.Electrophoresis · 2023Review
- Synthesis of Stereoenriched Piperidines via Chemo-Enzymatic Dearomatization of Activated Pyridines.Journal of the American Chemical Society · 2022Article
- Photo and copper dual catalysis for allene syntheses from propargylic derivatives via one-electron process.Nature communications · 2022Article
- Catalytic Asymmetric β-Oxygen Elimination.Angewandte Chemie (International ed. in English) · 2022Article
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5 authors.
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Abstract
Herein we report the copper-catalyzed silylation of propargylic difluorides to generate axially chiral, tetrasubstituted monofluoroallenes in both good yields (27 examples >80%) and enantioselectivities (82-98% ee). Compared to previously reported synthetic routes to axially chiral allenes (ACAs) from prochiral substrates, a mechanistically distinct reaction has been developed: the enantiodiscrimination between enantiotopic fluorides to set an axial stereocenter. DFT calculations and vibrational circular dichroism (VCD) suggest that β-fluoride elimination from an alkenyl copper intermediate likely proceeds through a
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