ArticleAngewandte Chemie (International ed. in English)2020
Stereodivergent Alkyne Hydrofluorination Using Protic Tetrafluoroborates as Tunable Reagents.
Article in Angewandte Chemie (International ed. in English), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
15 citing papers in PubMed, 56 citations in OpenAlex.
- Visible-Light-Induced Carbon-Hydrogen Phosphonylation of Conjugated Polymers via Electron Donor-Acceptor Complex Activation.Angewandte Chemie (International ed. in English) · 2026Article
- AgBFChemical science · 2026Article
- Platinum-Catalysed Hydrofluorination of Alkynes at Room Temperature Promoted by a Fluoride Shuttle.Angewandte Chemie (International ed. in English) · 2025Article
- The stereo-divergent functionalization of alkynes: a comprehensive review.RSC advances · 2025Review
- Stereodivergent Palladium-Catalyzed C-F Bond Functionalization ofOrganic letters · 2024Article
- Observation of unusual outer-sphere mechanism using simple alkenes as nucleophiles in allylation chemistry.Nature communications · 2024Article
- The "cesium effect" magnified: exceptional chemoselectivity in cesium ion mediated nucleophilic reactions.Chemical science · 2024Article
- Article
- Synthetic Advantages of Defluorinative C-F Bond Functionalization.Angewandte Chemie (International ed. in English) · 2023Review
- Regioselective Electrophilic Addition to Propargylic B(MIDA)s Enabled by β-Boron Effect.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2023Article
- Divergent Functionalization of Alkynes Enabled by Organic Photoredox Catalysis.Synlett : accounts and rapid communications in synthetic organic chemistry · 2023Article
- Vinyl cation-mediated intramolecular hydroarylation of alkynes using pyridinium reagents.Chemical communications (Cambridge, England) · 2022Article
- Platinum-Catalyzed Hydrofluorination of Alkynes: Hydrogen Bonding to Indolylphosphine Ligands to Provide Fluoride Reactivity.Angewandte Chemie (International ed. in English) · 2022Article
- Charge-State Dependence of Proton Uptake in Polyoxovanadate-alkoxide Clusters.Inorganic chemistry · 2022Article
- Au(I) Catalyzed HF Transfer: Tandem Alkyne Hydrofluorination and Perfluoroarene Functionalization.ACS catalysis · 2022Article
Corrections and comments
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Authors and funding
7 authors at 1 institution in 1 country.
Funding
Abstract
The discovery of safe, general, and practical procedures to prepare vinyl fluorides from readily available precursors remains a synthetic challenge. The metal-free hydrofluorination of alkynes constitutes an attractive though elusive strategy for their preparation. Introduced here is an inexpensive and easily handled reagent that enables the development of simple and scalable protocols for the regioselective hydrofluorination of alkynes to access both the E and Z isomers of vinyl fluorides. These reaction conditions were suitable for a diverse collection of alkynes, including several highly functionalized pharmaceutical derivatives. Computational and experimental mechanistic studies support C-F bond formation through vinyl cation intermediates, with the E- and Z-hydrofluorination products forming under kinetic and thermodynamic control, respectively.
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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.