ArticleAngewandte Chemie (International ed. in English)2017
Transition-Metal-Free C3 Arylation of Indoles with Aryl Halides.
Article in Angewandte Chemie (International ed. in English), 2017. 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.
- Article
- Metal-free molecular editing of indole via tandem reaction: Access to 2-aryl-3-aryldiazenylindole for theranostic applications.iScience · 2025Article
- Unveiling the Significance of tert-Butoxides in Transition Metal-Free Cross-Coupling Reactions.Topics in current chemistry (Cham) · 2024Review
- Activation of perfluoroalkyl iodides by anions: extending the scope of halogen bond activation to C(spChemical science · 2023Article
- Nucleophilic C4-selective (hetero) arylation of pyridines for facile synthesis of heterobiaryls.Frontiers in chemistry · 2023Article
- Substituent Effects and the Energetics of Noncatalyzed Aryl Halide Aminations: A Theoretical Investigation.ACS omega · 2021Article
- Recent Progress Concerning theMolecules (Basel, Switzerland) · 2021Review
- Polarclean/Water as a Safe and Recoverable Medium for Selective C2-Arylation of Indoles Catalyzed by Pd/C.ACS sustainable chemistry & engineering · 2020Article
- Nucleophile-intercepted Beckmann fragmentation reactions.Chemical science · 2019Article
- Catalytic Au(i)/Au(iii) arylation with the hemilabile MeDalphos ligand: unusual selectivity for electron-rich iodoarenes and efficient application to indoles.Chemical science · 2019Article
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Authors and funding
2 authors.
Funding
Abstract
We report an unprecedented transition metal-free coupling of indoles with aryl halides. The reaction is promoted by KOtBu and is regioselective for C3 over N. The use of degassed solvents devoid of oxygen is necessary for the success of the transformation. Preliminary studies implicate a hybrid mechanism that involves both aryne intermediates and non-propagative radical processes. Electron transfer is also a distinct possibility. These conclusions were substantiated by EPR data, isotopic labeling studies, and the use of radical scavengers and electron transfer inhibitors.
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