ArticleAngewandte Chemie (International ed. in English)2016
Palladium-Catalyzed Defluorinative Coupling of 1-Aryl-2,2-Difluoroalkenes and Boronic Acids: Stereoselective Synthesis of Monofluorostilbenes.
Article in Angewandte Chemie (International ed. in English), 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 26 papers.
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Who cites it
26 citing papers in PubMed.
- Stereoselective Synthesis of Alkenyl Fluorides and Alkynes by Defluoro Coupling of Trifluoromethyl Arenes.Angewandte Chemie (International ed. in English) · 2025Article
- Monodefluorinative Halogenation of Perfluoroalkyl Ketones via Organophosphorus-Mediated Selective C-F Activation.JACS Au · 2025Article
- Stereodivergent Palladium-Catalyzed C-F Bond Functionalization ofOrganic letters · 2024Article
- C-H and C-F bond activation of fluorinated propenes at Rh: enabling cross-coupling reactions with outer-sphere C-C coupling.Chemical science · 2024Article
- Synthetic Advantages of Defluorinative C-F Bond Functionalization.Angewandte Chemie (International ed. in English) · 2023Review
- Stereoselective Palladium-Catalyzed C-F Bond Alkenylation of TetrasubstitutedOrganic letters · 2023Article
- Homogeneous Organic Electron Donors in Nickel-Catalyzed Reductive Transformations.The Journal of organic chemistry · 2022Review
- Synergistic Pd/Cu-catalyzed enantioselective CspNature communications · 2022Article
- Palladium-catalysed difluoroolefination of benzyl tosylates toward the synthesis ofRSC advances · 2022Article
- Synthesis of bioactive fluoropyrrolidinesChemical science · 2022Article
- Ligand-controlled regioselective and chemodivergent defluorinative functionalization ofChemical science · 2021Article
- Generation of Axially Chiral Fluoroallenes through a Copper-Catalyzed Enantioselective β-Fluoride Elimination.Journal of the American Chemical Society · 2021Article
- Arylation ofChemical science · 2020Article
- Copper-Catalyzed Defluorinative Borylation and Silylation ofOrganic letters · 2020Article
- Cobalt-Catalyzed Selective Unsymmetrical Dioxidation ofThe Journal of organic chemistry · 2020Article
- Selective Quadruple C(spiScience · 2020Article
- Article
- Synthesis of gem-Difluoro Olefins through C-H Functionalization and β-fluoride Elimination Reactions.Angewandte Chemie (International ed. in English) · 2020Article
- Organocatalytic Strategy for Hydrophenolation ofTetrahedron · 2019Article
- Enantioselective construction of remote tertiary carbon-fluorine bonds.Nature chemistry · 2019Article
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2 authors.
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Abstract
The palladium-catalyzed defluorinative coupling of 1-aryl-2,2-difluoroalkenes with boronic acids is described. Broad functional-group tolerance arises from a redox-neutral process by a palladium(II) active species which is proposed to undergo a β-fluoride elimination to afford the products. The monofluorostilbene products were formed with excellent diastereoselectivity (≥50:1) in all cases, and it is critical, as traditional chromatographic techniques often fail to separate monofluoroalkene isomers. As a demonstration of this method's unique combination of reactivity and functional-group tolerance, a Gleevec® analogue, using a monofluorostilbene as an amide isostere, was synthesized.
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