ArticleOrganic letters2017
Palladium-Catalyzed, Enantioselective α-Arylation of α-Fluorooxindoles.
Article in Organic letters, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed, 88 citations in OpenAlex.
- Approach Toward Stereoselective α-Arylation by Pd/Cu-Catalyzed Arylboration of Electron Deficient Alkenes.Angewandte Chemie (International ed. in English) · 2025Article
- Organocatalytic Asymmetric Conjugate Addition of Fluorooxindoles to Quinone Methides.The Journal of organic chemistry · 2024Article
- Enantioseparation and racemization of 3-fluorooxindoles.Chirality · 2023Article
- Direct Observation of Diastereomeric α-C-Bound Enolates during Enantioselective α-Arylations: Synthesis, Characterization, and Reactivity of Arylpalladium Fluorooxindole Complexes.Journal of the American Chemical Society · 2021Article
- α-C(spNatural products and bioprospecting · 2021Review
- Accounting for Strong Ligand Sensitivity in Pd-Catalyzed α-Arylation of Enolates from Ketones, Esters, and Nitroalkanes.The Journal of organic chemistry · 2020Article
- Transition-metal-free α-arylation of oxindolesChemical science · 2019Article
- Amide Activation in Ground and Excited States.Molecules (Basel, Switzerland) · 2018Article
- Modern Approaches for Asymmetric Construction of Carbon-Fluorine Quaternary Stereogenic Centers: Synthetic Challenges and Pharmaceutical Needs.Chemical reviews · 2018Review
- Organocatalytic Stereoselective Synthesis of Fluorinated 3,3'-Linked Bisoxindoles.The Journal of organic chemistry · 2018Article
- Organocatalytic Asymmetric Synthesis of α-Oxetanyl and α-Azetidinyl Tertiary Alkyl Fluorides and Chlorides.Organic letters · 2018Article
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
Transition-metal-catalyzed asymmetric α-arylation of carbonyl compounds is a widely studied method for C-C bond formation. Recently, the α-arylation of α-fluoro ketones has been reported, including enantioselective α-arylation of α-fluoro ketones. However, the asymmetric α-arylation of α-fluoro carbonyl compounds in the carboxylic acid oxidation state has not been reported. We report the enantioselective α-arylation of α-fluorooxindoles with aryl triflates. The reaction occurs in high yield and with high enantioselectivity when catalyzed by a Pd-Segphos complex. This general class of product serves as an enantioenriched, nonenolizable version of α-aryl oxindoles.
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