ArticleNature chemistry2023
A C-H activation-based enantioselective synthesis of lower carbo[n]helicenes.
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 21 papers.
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Who cites it
21 citing papers in PubMed.
- Stereoselective synthesis of E-shaped double helicene analogues via organocatalytic intermolecular cycloaddition.Nature communications · 2026Article
- Adaptive Cavity-Enabled Crystalline Chirality in Nanocarbon Cages.Angewandte Chemie (International ed. in English) · 2026Article
- Biomimetic all-metal PdScience advances · 2026Article
- Skeletal rearrangement of [4]helicenes under acidic conditions: dynamic chirality and improved properties by subsequent peripheral editing.Chemical science · 2026Article
- Asymmetric Catalysis: Recent Advances toward a More Sustainable Synthesis.ACS central science · 2026Review
- Intermolecular Enantioselective Nickel-Catalyzed Arylation of Un-Activated C(spAngewandte Chemie (International ed. in English) · 2026Article
- Enantiotopic-group-selective coupling for unified access to carbazole atropisomers as versatile chiral chromophores.Nature communications · 2025Article
- Chiral Dysprosium-[7]Helicene Macrocycles Showing Record Single-Molecule Magnet Properties in the Lanthanide-Helicene Family.Journal of the American Chemical Society · 2025Article
- Quantum Chemistry Calculations of Circularly Polarized Luminescence (CPL): From Spectral Modeling to Molecular Design.Chemical reviews · 2025Review
- Acid/Base-Responsive Circularly Polarized Luminescence Emitters with Configurationally Stable Nitrogen Stereogenic Centers.Advanced materials (Deerfield Beach, Fla.) · 2025Article
- Two-photon Excitation of Bright Diaza[4]Helicenes for Isotropic and Circularly Polarized Emission.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Enantiomer-enriched π-extended helicenes with a perylene core from binaphthol: axial-to-helical chirality transfer with a stepwise Scholl reaction mechanism.Chemical science · 2025Article
- Asymmetric S=N-embedded polyaromatic construction via enantioselective Pd-catalyzed C-H activation.Nature communications · 2025Article
- Control of Dynamic Chirality in Donor-Acceptor Fluorophores.Angewandte Chemie (International ed. in English) · 2025Article
- Organocatalytic enantioselective synthesis of double S-shaped quadruple helicene-like molecules.Nature communications · 2025Article
- Accessing carbon, boron and germanium spiro stereocentres in a unified catalytic enantioselective approach.Nature catalysis · 2025Article
- Catalytic kinetic resolution of helical polycyclic phenols via an organocatalyzed enantioselective dearomative amination reaction.Science advances · 2024Article
- Chiral dinitrogen ligand enabled asymmetric Pd/norbornene cooperative catalysis toward the assembly of C-N axially chiral scaffolds.Nature communications · 2024Article
- Access to chiral dihydrophenanthridinesChemical science · 2024Article
- Enantioselective synthesis of [4]helicenes by organocatalyzed intermolecular C-H amination.Nature communications · 2024Article
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Abstract
The three-dimensional structure of carbohelicenes has fascinated generations of molecular chemists and has been exploited in a wide range of applications. Their strong circularly polarized luminescence has attracted considerable attention in recent years due to promising applications in new optical materials. Although the enantioselective synthesis of fused carbo- and heterohelicenes has been achieved, a direct catalytic enantioselective method allowing the synthesis of lower, non-fused carbo[n]helicenes (n = 4-6) is still lacking. We report here that Pd-catalysed enantioselective C-H arylation in the presence of a unique bifunctional phosphine-carboxylate ligand provides a simple and general access to these lower carbo[n]helicenes. Computational mechanistic studies indicate that both the C-H activation and reductive elimination steps contribute to the overall enantioselectivity. The observed enantio-induction seems to arise from a combination of non-covalent interactions and steric repulsion between the substrate and ligand during the two key reductive elimination steps. The photophysical and chiroptical properties of the synthesized scalemic [n]helicenes have been systematically studied.
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