ArticleChemical science2020
Radical α-addition involved electrooxidative [3 + 2] annulation of phenols and electron-deficient alkenes.
Article in Chemical science, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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8 citing papers in PubMed.
- Synthesis of 5-(pyrazol-4-yl) pentanoic acids and 4-(pyrazol-4-yl) butanoic acidsRSC advances · 2025Article
- Visible-light TiOChemical science · 2024Article
- Selective Cleavage of Lignin Model Compounds via a Reverse Biosynthesis Mechanism.Organic letters · 2023Article
- Photocatalyzed regioselective hydrosilylation for the divergent synthesis of geminal and vicinal borosilanes.Nature communications · 2023Article
- Catalytic Oxidative Coupling of Phenols and Related Compounds.ACS catalysis · 2022Article
- Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.Chemical reviews · 2022Review
- Oxidative Photocatalytic Homo- and Cross-Coupling of Phenols: Nonenzymatic, Catalytic Method for Coupling Tyrosine.ACS catalysis · 2020Article
- Formal oxo- and aza-[3 + 2] reactions of α-enaminones and quinones: a double divergent process and the roles of chiral phosphoric acid and molecular sieves.Chemical science · 2020Article
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5 authors.
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Abstract
An electrooxidative [3 + 2] annulation of phenols and electron-deficient alkenes for the synthesis of C3-functionalized 2-aryl-2,3-dihydrobenzofuran derivatives was achieved. The ring construction starts by a unique α-addition of carbon radicals derived from anodic oxidation of phenols to electron-deficient alkenes. The subsequent anodic oxidation of the resulting alkyl radical intermediates followed by trapping with the phenolic hydroxy group assembles the 2,3-dihydrobenzofuran core. Such a pathway enables the installation of various electrophilic functionalities including alkoxycarbonyl, alkylaminocarbonyl, trifluoromethyl, and cyano groups at the C-3 of the 2,3-dihydrobenzofuran framework, which is unattainable by other intermolecular reactions. The application of this method for a rapid synthesis of a bioactive natural product is demonstrated.
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