ArticleNature chemistry2018
Organocatalytic asymmetric arylation of indoles enabled by azo groups.
Article in Nature chemistry, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 50 papers.
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Who cites it
50 citing papers in PubMed, 357 citations in OpenAlex.
- Enantioselective Rh-catalyzed addition of indoles to enones and the key role of the free N-H group with acyclic enones.Chemical science · 2026Article
- Catalytic asymmetric formal nucleophilic C2-substitution of indoles via C2-umpolung toward 2,3'-bisindole atropisomers.Nature communications · 2026Article
- Propellane Alkaloid Biosynthesis and Total Synthesis via Interrupted Reaction Pathways.ACS central science · 2026Article
- Copper-Catalyzed Asymmetric Cyclizative Sulfinamidation: Forging Indole-Based Stereogenic Sulfur(IV) Centers and Atropisomeric Chirality.ACS central science · 2025Article
- Atroposelective Synthesis of Azobenzenes by Palladium-Catalyzed Cross-Coupling of Racemic Biaryl Triflates and Diazenyl Pronucleophiles.Journal of the American Chemical Society · 2025Article
- Organocatalytic Enantioselective Friedel-Crafts Reaction of Phenanthrenequinones and Indoles.Molecules (Basel, Switzerland) · 2025Article
- Gold-Catalyzed Diyne-Ene Annulation for the Synthesis of Polysubstituted Benzenes through Formal [3+3] Approach with Amide as the Critical Co-Catalyst.Angewandte Chemie (International ed. in English) · 2024Article
- Atroposelective catalysis.Nature reviews. Chemistry · 2024Review
- Tunable molecular editing of indoles with fluoroalkyl carbenes.Nature chemistry · 2024Article
- Catalytic Asymmetric Diastereodivergent Synthesis of 2-Alkenylindoles Bearing both Axial and Central Chirality.Precision chemistry · 2024Article
- Pd-catalyzed asymmetric Larock reaction for the atroposelective synthesis of N─N chiral indoles.Science advances · 2024Article
- Catalytic Enantioselective Synthesis of Axially Chiral Imidazoles by Cation-Directed Desymmetrization.Journal of the American Chemical Society · 2023Article
- Diversity-Oriented Catalytic Asymmetric Dearomatization of Indoles with o-Quinone Diimides.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2023Article
- Dynamic Kinetic Resolution of Indole-Based Sulfenylated Heterobiaryls by Rhodium-Catalyzed Atroposelective Reductive Aldol Reaction.ACS catalysis · 2023Article
- Asymmetric Synthesis of Axially Chiral Molecules via Organocatalytic Cycloaddition and Cyclization Reactions.Molecules (Basel, Switzerland) · 2023Review
- Asymmetric rhodium-catalyzed click cycloaddition to access C-N axially chiralChemical science · 2023Article
- Enantioselective Synthesis of Atropisomers by Oxidative Aromatization with Central-to-Axial Conversion of Chirality.Molecules (Basel, Switzerland) · 2023Review
- Enantioselective construction of triaryl-substituted all-carbon quaternary stereocentersChemical science · 2023Article
- Design and synthesis of axially chiral aryl-pyrroloindoles via the strategy of organocatalytic asymmetric (2 + 3) cyclization.Fundamental research · 2023Article
- Enantioselective synthesis of atropisomeric indoles via iron-catalysed oxidative cross-coupling.Nature chemistry · 2023Article
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Arylation is a fundamental reaction that can be mostly fulfilled by electrophilic aromatic substitution and transition-metal-catalysed aryl functionalization. Although the azo group has been used as a directing group for many transformations via transition-metal-catalysed aryl carbon-hydrogen (C-H) bond activation, there remain significant unmet challenges in organocatalytic arylation. Here, we show that the azo group can effectively act as both a directing and activating group for organocatalytic asymmetric arylation of indoles via formal nucleophilic aromatic substitution of azobenzene derivatives. Thus, a wide range of axially chiral arylindoles have been achieved in good yields with excellent enantioselectivities by utilizing chiral phosphoric acid as catalyst. Furthermore, highly enantioenriched pyrroloindoles bearing two contiguous quaternary chiral centres have also been obtained via a cascade enantioselective formal nucleophilic aromatic substitution-cyclization process. This strategy should be useful in other related research fields and will open new avenues for organocatalytic asymmetric aryl functionalization.
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