ArticleNature chemistry2023
Enantioselective synthesis of atropisomeric indoles via iron-catalysed oxidative cross-coupling.
Article in Nature chemistry, 2023. 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.
- Installing Axial Chirality by Atroposelective C(spJournal of the American Chemical Society · 2026Article
- Direct Arylation of Unactivated Arenes Using Earth-Abundant Iron/Tetra-Aza Macrocyclic Complexes.Inorganic chemistry · 2026Article
- Copper-Catalyzed Asymmetric Cyclizative Sulfinamidation: Forging Indole-Based Stereogenic Sulfur(IV) Centers and Atropisomeric Chirality.ACS central science · 2025Article
- Atroposelective catalysis.Nature reviews. Chemistry · 2024Review
- Catalytic Asymmetric Diastereodivergent Synthesis of 2-Alkenylindoles Bearing both Axial and Central Chirality.Precision chemistry · 2024Article
- 1,5-Hydrogen atom transfer of α-iminyl radical cations: a new platform for relay annulation for pyridine derivatives and axially chiral heterobiaryls.Chemical science · 2024Article
- Pd-catalyzed asymmetric Larock reaction for the atroposelective synthesis of N─N chiral indoles.Science advances · 2024Article
- Iron-catalyzed stereoselective C-H alkylation for simultaneous construction of C-N axial and C-central chirality.Nature communications · 2024Article
- Dynamic Kinetic Resolution of Indole-Based Sulfenylated Heterobiaryls by Rhodium-Catalyzed Atroposelective Reductive Aldol Reaction.ACS catalysis · 2023Article
- Axially chiral styrene-based organocatalysts and their application in asymmetric cascade Michael/cyclization reaction.Chemical science · 2023Article
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Authors and funding
5 authors.
Funding
Abstract
Heterobiaryl compounds that exhibit axial chirality are of increasing value and interest across several fields, but direct oxidative methods for their enantioselective synthesis remain elusive. Here we disclose that an iron catalyst in the presence of a chiral PyBOX ligand and an oxidant enables direct coupling between naphthols and indoles to yield atropisomeric heterobiaryl compounds with high levels of enantioselectivity. The reaction exhibits remarkable chemoselectivity and exclusively yields cross-coupled products without competing homocoupling. Mechanistic investigations enable us to postulate that an indole radical is generated in the reaction but that this is probably an off-cycle event, and that the reaction proceeds through formation of a chiral Fe-bound naphthoxy radical that is trapped by a nucleophilic indole. We envision that this simple, cheap and sustainable catalytic manifold will facilitate access to a range of heterobiaryl compounds and enable their application across the fields of materials science, medicinal chemistry and catalysis.
Identifiers
36509852What OpenQuestion holds
Registered trials
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