ArticleNature chemistry2017
Asymmetric silver-catalysed intermolecular bromotrifluoromethoxylation of alkenes with a new trifluoromethoxylation reagent.
Article in Nature chemistry, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 25 papers.
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Who cites it
25 citing papers in PubMed, 154 citations in OpenAlex.
- Intertwined Processes in the Pummerer-Type Rearrangement Affording α-Trifluoromethoxylated Thioethers and the Corresponding Highly Enantioenriched Sulfoxides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- An anion-binding approach to enantioselective photoredox catalysis.Science (New York, N.Y.) · 2025Article
- Assessing Fluorosulfonyl Pentafluorooxosulfate (FSOAngewandte Chemie (International ed. in English) · 2025Article
- N-Heterocyclic Carbene Organocatalysis Enabled Modular Synthesis of Fluorinated Isoflavonoids to Suppress Proliferation and Migration in Breast Cancer Cells.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025Article
- Compact Disc-Derived Nanocarbon-Supported Catalysts with Extreme Catalytic Activity.ACS applied materials & interfaces · 2025Article
- Halo-perfluoroalkoxylation ofChemical science · 2024Article
- Fluorocarbonylation via palladium/phosphine synergistic catalysis.Nature communications · 2023Article
- Radical α-Trifluoromethoxylation of Ketones under Batch and Flow Conditions by Means of Organic Photoredox Catalysis.Organic letters · 2021Article
- Synthetic exploration of sulfinyl radicals using sulfinyl sulfones.Nature communications · 2021Article
- Trifluoromethyl Nonaflate: A Practical Trifluoromethoxylating Reagent and its Application to the Regio- and Stereoselective Synthesis of Trifluoromethoxylated Alkenes.Angewandte Chemie (International ed. in English) · 2021Article
- Catalytic enantioselective bromohydroxylation of cinnamyl alcohols.RSC advances · 2021Article
- Metal-free visible-light-enabled vicinal trifluoromethyl dithiolation of unactivated alkenes.Beilstein journal of organic chemistry · 2021Article
- Selective C-H trifluoromethoxylation of (hetero)arenes as limiting reagent.Nature communications · 2020Article
- Regio- and Stereoselective Thianthrenation of Olefins To Access Versatile Alkenyl Electrophiles.Angewandte Chemie (International ed. in English) · 2020Article
- Oxidation of difluorocarbene and subsequent trifluoromethoxylation.Nature communications · 2019Article
- Enantioselective Benzylation and Allylation of α-Trifluoromethoxy Indanones under Phase-Transfer Catalysis.Molecules (Basel, Switzerland) · 2019Article
- α-Fluorination of carbonyls with nucleophilic fluorine.Nature chemistry · 2019Article
- Silver-mediated oxidative functionalization of alkylsilanes.Chemical science · 2018Article
- Recent Development of Catalytic Trifluoromethoxylation Reactions.Tetrahedron · 2018Article
- Redox-Active Reagents for Photocatalytic Generation of the OCFAngewandte Chemie (International ed. in English) · 2018Article
Corrections and comments
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Authors and funding
5 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Fluorinated organic compounds are becoming increasingly important in pharmaceuticals, agrochemicals and materials science. The introduction of trifluoromethoxy groups into new drugs and agrochemicals has attracted much attention due to their strongly electron-withdrawing nature and high lipophilicity. However, synthesis of trifluoromethoxylated organic molecules is difficult owing to the decomposition of trifluoromethoxide anion and β-fluoride elimination from transition-metal-trifluoromethoxide complexes, and no catalytic enantioselective trifluoromethoxylation reaction has been reported until now. Here, we present an example of an asymmetric silver-catalysed intermolecular bromotrifluoromethoxylation of alkenes with trifluoromethyl arylsulfonate (TFMS) as a new trifluoromethoxylation reagent. Compared to other trifluoromethoxylation reagents, TFMS is easily prepared and thermally stable with good reactivity. In addition, this reaction is operationally simple, scalable and proceeds under mild reaction conditions. Furthermore, broad scope and good functional group compatibility has been demonstrated by application of the method to the bromotrifluoromethoxylation of double bonds in natural products and natural product derivatives.
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