ArticleNature communications2020
Electrooxidation enables highly regioselective dearomative annulation of indole and benzofuran derivatives.
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 14 papers.
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Who cites it
14 citing papers in PubMed.
- Enantioselective Rh-catalyzed addition of indoles to enones and the key role of the free N-H group with acyclic enones.Chemical science · 2026Article
- Electrochemically driven strain-release dearomative (3 + 2) cyclization for the synthesis of bicyclo[2.1.1]hexane-fused polycyclic spiroindolines.Chemical science · 2026Article
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- Article
- Mechanistic duality of indolyl 1,3-heteroatom transposition.Chemical science · 2023Article
- Aqueous Flavin Photoredox Catalysis Drives Exclusive C3-Alkylation of Indolyl Radical Cations in Route to Unnatural Tryptophan Mimetics.Organic letters · 2023Article
- Copper-catalyzed oxidative dehydrogenative dearomatization of indole derivatives: A new strategy to construct spirocyclic indolenines.iScience · 2022Article
- Dearomative (3+2) Cycloadditions between Indoles and Vinyldiazo Species Enabled by a Red-Shifted Chromium Photocatalyst.Angewandte Chemie (International ed. in English) · 2022Article
- Electrochemical oxidative rearrangement of tetrahydro-β-carbolines in a zero-gap flow cell.Chemical science · 2022Article
- Selective skeletal editing of polycyclic arenes using organophotoredox dearomative functionalization.Nature communications · 2022Article
- Hypoiodite-Catalyzed Oxidative Umpolung of Indoles for Enantioselective Dearomatization.Journal of the American Chemical Society · 2022Article
- Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.Chemical reviews · 2022Review
- Organophotocatalytic dearomatization of indoles, pyrroles and benzo(thio)furans via a Giese-type transformation.Communications chemistry · 2021Article
- Dearomative [3 + 2] cycloaddition reaction of nitrobenzothiophenes with nonstabilized azomethine ylides.RSC advances · 2020Article
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Authors and funding
10 authors.
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Abstract
The dearomatization of arenes represents a powerful synthetic methodology to provide three-dimensional chemicals of high added value. Here we report a general and practical protocol for regioselective dearomative annulation of indole and benzofuran derivatives in an electrochemical way. Under undivided electrolytic conditions, a series of highly functionalized five to eight-membered heterocycle-2,3-fused indolines and dihydrobenzofurans, which are typically unattainable under thermal conditions, can be successfully accessed in high yield with excellent regio- and stereo-selectivity. This transformation can also tolerate a wide range of functional groups and achieve good efficiency in large-scale synthesis under oxidant-free conditions. In addition, cyclic voltammetry, electron paramagnetic resonance (EPR) and kinetic studies indicate that the dehydrogenative dearomatization annulations arise from the anodic oxidation of indole into indole radical cation, and this process is the rate-determining step.
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