ArticleNature communications2020
Direct transfer of tri- and di-fluoroethanol units enabled by radical activation of organosilicon reagents.
Article in Nature communications, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed.
- Nickel-catalyzed hydroxymethylation with α-siliconChemical science · 2026Article
- Uncovering outer-sphere mechanisms governing chemoselectivity in copper-photocatalyzed ATRA reactions of CFChemical science · 2026Article
- Trifluoromethylative and Pentafluoroethylative Heterofunctionalization (C-O, C-S, and C-N) of Alkenes Using Visible Light Photocatalysis.ACS omega · 2024Article
- Synthesis of constrained bicycloalkanes through bibase-promoted brook rearrangement/radical-polar crossover cyclization.Chemical science · 2024Article
- Synthetic utility of functionalized alkylsilyl peroxides for Fe-catalyzed and visible-light-promoted radical transformation.Chemical science · 2024Article
- Nickel-Catalyzed Suzuki-Miyaura Coupling in Water for the Synthesis of 2-Aryl Allyl Phosphonates and Sulfones.The Journal of organic chemistry · 2024Article
- Direct Synthesis of α-Aryl-α-Trifluoromethyl Alcohols via Nickel Catalyzed Cross-Electrophile Coupling.Angewandte Chemie (International ed. in English) · 2022Article
- Cascade cyclization of alkene-tethered acylsilanes and allylic sulfones enabled by unproductive energy transfer photocatalysis.Nature communications · 2022Article
- Tuning the reactivity of alkoxyl radicals from 1,5-hydrogen atom transfer to 1,2-silyl transfer.Nature communications · 2021Article
- Organocatalytic Synthesis of α-Trifluoromethyl Allylboronic Acids by Enantioselective 1,2-Borotropic Migration.Journal of the American Chemical Society · 2020Article
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8 authors.
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Abstract
Trifluoroethanol and difluoroethanol units are important motifs in bioactive molecules, but the methods to direct incorporate these units are limited. Herein, we report two organosilicon reagents for the transfer of trifluoroethanol and difluoroethanol units into molecules. Through intramolecular C-Si bond activation by alkoxyl radicals, these reagents were applied in allylation, alkylation and alkenylation reactions, enabling efficient synthesis of various tri(di)fluoromethyl group substituted alcohols. The broad applicability and general utility of the approach are highlighted by late-stage introduction of these fluoroalkyl groups to complex molecules, and the synthesis of antitumor agent Z and its difluoromethyl analog Z'.
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