ArticleChemistry (Weinheim an der Bergstrasse, Germany)2021
Neutral Chiral Tetrakis-Iodo-Triazole Halogen-Bond Donor for Chiral Recognition and Enantioselective Catalysis.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed.
- Neutral chiral bidentate tellurium-triazoles for enantioselective non-covalent chalcogen-bonding catalysis.Nature communications · 2026Article
- Highly Enantioselective Organocatalysis with Bidentate Halogen Bond Donors.Angewandte Chemie (International ed. in English) · 2025Article
- Asymmetric Counteranion-Directed Halogen Bonding Catalysis.Journal of the American Chemical Society · 2025Article
- Enhanced enantioselectivity in halogen-bonding catalysis.Communications chemistry · 2023Article
- Gauging the Strength of the Molecular Halogen Bond via Experimental Electron Density and Spectroscopy.ACS omega · 2023Article
- Enantioselective dearomatization reactions of heteroarenes by anion-binding organocatalysis.Chemical communications (Cambridge, England) · 2023Review
- Stereoselective Processes Based on σ-Hole Interactions.Molecules (Basel, Switzerland) · 2022Review
- N-Heterocyclic Iod(az)olium Salts - Potent Halogen-Bond Donors in Organocatalysis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Enantioselective Michael addition to vinyl phosphonatesChemical science · 2021Article
- Neutral Chiral Tetrakis-Iodo-Triazole Halogen-Bond Donor for Chiral Recognition and Enantioselective Catalysis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Halides as versatile anions in asymmetric anion-binding organocatalysis.Beilstein journal of organic chemistry · 2021Review
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Authors and funding
5 authors.
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Abstract
Halogen bonding represents a powerful tool in the field of noncovalent interactions. However, applications in enantioselective recognition and catalysis remain almost nonexistent, due in part to the distinct features of halogen bonds, including long covalent and noncovalent bond distances and high directionality. Herein, this work presents a novel chiral tetrakis-iodo-triazole structure as a neutral halogen bond donor for both chiral anion-recognition and enantioinduction in ion-pair organocatalysis. NMR-titration studies revealed significant differences in anion affinity between the halogen bonding receptor and its hydrogen bonding parent. Selective recognition of chiral dicarboxylates and asymmetric induction in a benchmark organocatalytic reaction were demonstrated using the halogen bond donor. Inversions in the absolute sense of chiral recognition, enantioselectivity, and chiroptical properties relative to the related hydrogen donor were observed. Computational modeling suggested that these effects were the result of distinct anion-binding modes for the halogen- versus hydrogen-bond donors.
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