ArticleAngewandte Chemie (International ed. in English)2014
Mild silver-mediated geminal difluorination of styrenes using an air- and moisture-stable fluoroiodane reagent.
Article in Angewandte Chemie (International ed. in English), 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 30 papers.
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Who cites it
30 citing papers in PubMed.
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- Harnessing Phenonium Ions in Synthesis.Angewandte Chemie (International ed. in English) · 2025Review
- Preparation of a benziodazole-type iodine(III) compound and its application as a nitrating reagent for synthesis of furazans via a copper-catalyzed cascade process.Communications chemistry · 2024Article
- Catalytic 1,1-diazidation of alkenes.Nature communications · 2024Article
- Hydrogen-bond activation enables aziridination of unactivated olefins with simple iminoiodinanes.Beilstein journal of organic chemistry · 2024Article
- Oxidative fluorination with Selectfluor: A convenient procedure for preparing hypervalent iodine(V) fluorides.Beilstein journal of organic chemistry · 2024Article
- Predicting bond dissociation energies of cyclic hypervalent halogen reagents using DFT calculations and graph attention network model.Beilstein journal of organic chemistry · 2024Article
- Regioselective, catalytic 1,1-difluorination of enynes.Nature chemistry · 2023Article
- Catalytic, Regioselective 1,4-Fluorodifunctionalization of Dienes.Angewandte Chemie (International ed. in English) · 2023Article
- Skeletal Ring Contractions via I(I)/I(III) Catalysis: Stereoselective Synthesis ofACS catalysis · 2022Article
- Hypervalent iodine-mediated β-difluoroalkylboron synthesisChemical science · 2022Article
- Electrophilic Fluorination of Alkenes via Bora-Wagner-Meerwein Rearrangement. Access to β-Difluoroalkyl Boronates.Angewandte Chemie (International ed. in English) · 2021Article
- Expanding organofluorine chemical space: the design of chiral fluorinated isosteres enabled by I(i)/I(iii) catalysis.Chemical science · 2021Review
- Formation of synthetically relevant CFRSC advances · 2021Article
- Trifluorinated Tetralins via I(I)/I(III)-Catalysed Ring Expansion: Programming Conformation by [CHAngewandte Chemie (International ed. in English) · 2021Article
- Difluorination of α-(bromomethyl)styrenesChemical science · 2021Article
- A Chiral Pentafluorinated Isopropyl Group via Iodine(I)/(III) Catalysis.Angewandte Chemie (International ed. in English) · 2021Article
- Enantioselective Construction of Tertiary Fluoride Stereocenters by Organocatalytic Fluorocyclization.Journal of the American Chemical Society · 2020Article
- Trifluoromethylthiolation, Trifluoromethylation, and Arylation Reactions of Difluoro Enol Silyl Ethers.The Journal of organic chemistry · 2020Article
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Authors and funding
3 authors.
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Abstract
An air- and moisture-stable fluoroiodane in the presence of AgBF4 is suitable for selective geminal difluorination of styrenes under mild reaction conditions. One of the CF bonds is formed by transfer of electrophilic fluorine from the hypervalent iodine reagent, while the other one arises from the tetrafluoroborate counterion of silver. Deuterium-isotope-labelling experiments and rearrangement of methyl styrene substrates suggest that the reaction proceeds through a phenonium ion intermediate.
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