ArticleCommunications chemistry2021
Halogen-sodium exchange enables efficient access to organosodium compounds.
Article in Communications chemistry, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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Who cites it
19 citing papers in PubMed.
- Ligand- and alkali metal identity-effects in ligand-inducedChemical science · 2026Article
- Comparisons and Contrasts in a Complete Set of Alkali Metal Cumyl Structures.Inorganic chemistry · 2026Article
- Reactivity of a Sodium Anion with Alkenes: 1-Electron vs 2-Electron Reductions.Inorganic chemistry · 2025Article
- Isolation and reactivity of sodium benzyl cations.Nature communications · 2025Article
- Assessing Sodium Amide Reagents for Ester Amidations in Deep Eutectic Solvents in Continuous Flow.ACS sustainable chemistry & engineering · 2025Article
- Synthesis and Structure of Neopentyl Sodium: A Hydrocarbon-Soluble Reagent for Controlled Sodiation of Non-Activated Substrates.Angewandte Chemie (International ed. in English) · 2025Article
- Functionalization of Pyridines at the C4 Position via Metalation and Capture.Angewandte Chemie (International ed. in English) · 2025Article
- Iron-catalysed direct coupling of organosodium compounds.Nature synthesis · 2025Article
- The Application of Flow Chemistry for the Synthesis of Alkyl Sodium Compounds and Their Transformations with Weinreb Amides and Carboxylic Acids.Organic letters · 2024Article
- Mechanochemistry enabling highly efficient Birch reduction using sodium lumps and d-(+)-glucose.Chemical science · 2024Article
- Opportunities with calcium Grignard reagents and other heavy alkaline-earth organometallics.Nature reviews. Chemistry · 2023Review
- A fruitful century for the scalable synthesis and reactions of biphenyl derivatives: applications and biological aspects.RSC advances · 2023Review
- Li vs Na: Divergent Reaction Patterns between Organolithium and Organosodium Complexes and Ligand-Catalyzed Ketone/Aldehyde Methylenation.Journal of the American Chemical Society · 2023Article
- Sustainable and practical formation of carbon-carbon and carbon-heteroatom bonds employing organo-alkali metal reagents.Chemical science · 2023Review
- Sodium Isopropyl(trimethylsilyl)amide: A Stable and Highly Soluble Lithium Diisopropylamide Mimic.The Journal of organic chemistry · 2022Article
- Enhancing Metalating Efficiency of the Sodium Amide NaTMP in Arene Borylation Applications.Angewandte Chemie (International ed. in English) · 2022Article
- Sigma/pi Bonding Preferences of Solvated Alkali-Metal Cations to Ditopic Arylmethyl Anions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Review
- THF-solvated Heavy Alkali Metal Benzyl Compounds (Na, Rb, Cs): Defined Deprotonation Reagents for Alkali Metal Mediation Chemistry.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Ketone Enolization with Sodium Hexamethyldisilazide: Solvent- and Substrate-DependentJournal of the American Chemical Society · 2021Article
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5 authors.
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Abstract
With sodium being the most abundant alkali metal on Earth, organosodium compounds are an attractive choice for sustainable chemical synthesis. However, organosodium compounds are rarely used-and are overshadowed by organolithium compounds-because of a lack of convenient and efficient preparation methods. Here we report a halogen-sodium exchange method to prepare a large variety of (hetero)aryl- and alkenylsodium compounds including tri- and tetrasodioarenes, many of them previously inaccessible by other methods. The key discovery is the use of a primary and bulky alkylsodium lacking β-hydrogens, which retards undesired reactions, such as Wurtz-Fittig coupling and β-hydrogen elimination, and enables efficient halogen-sodium exchange. The alkylsodium is readily prepared in situ from neopentyl chloride and an easy-to-handle sodium dispersion. We believe that the efficiency, generality, and convenience of the present method will contribute to the widespread use of organosodium in organic synthesis, ultimately contributing to the development of sustainable organic synthesis by rivalling the currently dominant organolithium reagents.
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