ArticleAngewandte Chemie (International ed. in English)2021
Counterion Control of t-BuO-Mediated Single Electron Transfer to Nitrostilbenes to Construct N-Hydroxyindoles or Oxindoles.
Article in Angewandte Chemie (International ed. in English), 2021. 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.
- How Alkali Metal Alkoxides Initiate Organic Radical Reactions.Journal of the American Chemical Society · 2026Article
- Radical Formation by Direct Single Electron Transfer between Nitrobenzene and Anionic Organo Bases.ACS omega · 2025Article
- Harnessing the Reactivity of Nitroarene Radical Anions to Create Quinoline N-Oxides by Electrochemical Reductive Cyclization.Angewandte Chemie (International ed. in English) · 2025Article
- Intramolecular CH-Hydrogen Bonding During the Dissociation of the Oxaphosphetane Intermediate Facilitates Z/E-Selectivity in Wittig Olefination.ChemistryOpen · 2024Article
- A base-mediated synthesis ofTetrahedron · 2023Article
- Article
- Unlocking electrophilicSynlett : accounts and rapid communications in synthetic organic chemistry · 2022Article
- A switchable redox annulation of 2-nitroarylethanols affordingChemical science · 2022Article
- Recent Advances to Mediate Reductive Processes of Nitroarenes Using Single-Electron Transfer, Organomagnesium, or Organozinc Reagents.Synthesis · 2022Article
- Article
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Authors and funding
6 authors.
Funding
Abstract
tert-Butoxide unlocks new reactivity patterns embedded in nitroarenes. Exposure of nitrostilbenes to sodium tert-butoxide was found to produce N-hydroxyindoles at room temperature without an additive. Changing the counterion to potassium changed the reaction outcome to yield solely oxindoles through an unprecedented dioxygen-transfer reaction followed by a 1,2-phenyl migration. Mechanistic experiments established that these reactions proceed via radical intermediates and suggest that counterion coordination controls whether an oxindole or N-hydroxyindole product is formed.
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