ArticleNature communications2022
Catalytic atroposelective synthesis of axially chiral benzonitriles via chirality control during bond dissociation and CN group formation.
Article in Nature communications, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed.
- Access to C─N and N─N Axially Chiral Pyridinones via NHC-Catalyzed Dynamic Kinetic Resolution of Rotationally Restricted Cyclic Imides.Angewandte Chemie (International ed. in English) · 2026Article
- Atroposelective Construction of Axially Chiral Tetraarylethenes Via NHC-Catalyzed Desymmetrization.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- Theoretical studies on anhydride dynamic covalent bond exchange mechanisms.Communications chemistry · 2025Article
- Organocatalyzed atroposelective dynamic kinetic resolutions via transient seven-membered cyclic hemiacetals.Science advances · 2025Article
- Copper-catalysed dynamic kinetic asymmetric C-O cross-coupling to access chiral aryl oxime ethers and diaryl ethers.Nature communications · 2025Article
- Recent advances in organocatalytic atroposelective reactions.Beilstein journal of organic chemistry · 2025Review
- The first specific probe for pyrrolidine with multifunction by the interaction mechanism of atomic economic reaction.iScience · 2024Article
- Atroposelective catalysis.Nature reviews. Chemistry · 2024Review
- Synthesis of axially chiral diaryl ethersChemical science · 2024Article
- Atroposelective Synthesis of Aldehydes via Alcohol Dehydrogenase-Catalyzed Stereodivergent Desymmetrization.JACS Au · 2024Article
- Organocatalytic diastereo- and atroposelective construction of N-N axially chiral pyrroles and indoles.Nature communications · 2024Article
- Access to Axially Chiral Aryl Aldehydes via Carbene-Catalyzed Nitrile Formation and Desymmetrization Reaction.Research (Washington, D.C.) · 2024Article
- Facile access to benzofuran derivatives through radical reactions with heteroatom-centered super-electron-donors.Nature communications · 2023Article
- Enantioselective organocatalytic synthesis of axially chiral aldehyde-containing styrenes via SNature communications · 2023Article
- NHC-catalyzed enantioselective access to β-cyano carboxylic esters via in situ substrate alternation and release.Nature communications · 2023Article
- Chalcogen bond-guided conformational isomerization enables catalytic dynamic kinetic resolution of sulfoxides.Nature communications · 2022Article
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Authors and funding
6 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The applications of axially chiral benzonitriles and their derivatives remain mostly unexplored due to their synthetic difficulties. Here we disclose an unusual strategy for atroposelective access to benzonitriles via formation of the nitrile unit on biaryl scaffolds pre-installed with stereogenic axes in racemic forms. Our method starts with racemic 2-arylbenzaldehydes and sulfonamides as the substrates and N-heterocyclic carbenes as the organocatalysts to afford axially chiral benzonitriles in good to excellent yields and enantioselectivities. DFT calculations suggest that the loss of p-toluenesulfinate group is both the rate-determining and stereo-determining step. The axial chirality is controlled during the bond dissociation and CN group formation. The reaction features a dynamic kinetic resolution process modulated by both covalent and non-covalent catalytic interactions. The axially chiral benzonitriles from our method can be easily converted to a large set of functional molecules that show promising catalytic activities for chemical syntheses and anti-bacterial activities for plant protections.
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