ArticleMolecules (Basel, Switzerland)2019
Chiral Chalcogen Bond Donors Based on the 4,4'-Bipyridine Scaffold.
Article in Molecules (Basel, Switzerland), 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed, 40 citations in OpenAlex.
- Neutral chiral bidentate tellurium-triazoles for enantioselective non-covalent chalcogen-bonding catalysis.Nature communications · 2026Article
- Competing electrophilic substitution and oxidative polymerization of arylamines with selenium dioxide.Beilstein journal of organic chemistry · 2024Article
- Evidence for and evaluation of fluorine-tellurium chalcogen bonding.Chemical science · 2023Article
- Stereoselective Processes Based on σ-Hole Interactions.Molecules (Basel, Switzerland) · 2022Review
- On the Importance of Pnictogen and Chalcogen Bonding Interactions in Supramolecular Catalysis.International journal of molecular sciences · 2021Review
- Enantioseparation of 5,5'-Dibromo-2,2'-Dichloro-3-Selanyl-4,4'-Bipyridines on Polysaccharide-Based Chiral Stationary Phases: Exploring Chalcogen Bonds in Liquid-Phase Chromatography.Molecules (Basel, Switzerland) · 2021Article
- Factors Impacting σ- and π-Hole Regions as Revealed by the Electrostatic Potential and Its Source Function Reconstruction: The Case of 4,4'-Bipyridine Derivatives.Molecules (Basel, Switzerland) · 2020Article
- Rational Design, Synthesis, Characterization and Evaluation of Iodinated 4,4'-Bipyridines as New Transthyretin Fibrillogenesis Inhibitors.Molecules (Basel, Switzerland) · 2020Article
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Authors and funding
6 authors at 3 institutions in 3 countries.
Funding
Abstract
Organocatalysis through chalcogen bonding (ChB) is in its infancy, as its proof-of-principle was only reported in 2016. Herein, we report the design and synthesis of new chiral ChB donors, as well as the catalytic activity evaluation of the 5,5'-dibromo-2,2'-dichloro-3-((perfluorophenyl)selanyl)-4,4'-bipyridine as organocatalyst. The latter is based on the use of two electron-withdrawing groups, a pentafluorophenyl ring and a tetrahalo-4,4'-bipyridine skeleton, as substituents at the selenium center. Atropisomery of the tetrahalo-4,4'-bipyridine motif provides a chiral environment to these new ChB donors. Their synthesis was achieved through either selective lithium exchange and trapping or a site-selective copper-mediated reaction. Pure enantiomers of the 3-selanyl-4,4'-bipyridine were obtained by high performance liquid chromatography enantioseparation on specific chiral stationary phase, and their absolute configuration was assigned by comparison of the measured and calculated electronic circular dichroism spectra. The capability of the selenium compound to participate in σ-hole-based interactions in solution was studied by
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