ArticleAngewandte Chemie (International ed. in English)2021
(2-Ethylhexyl)sodium: A Hexane-Soluble Reagent for Br/Na-Exchanges and Directed Metalations in Continuous Flow.
Article in Angewandte Chemie (International ed. in English), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
19 citing papers in PubMed.
- Ligand- and alkali metal identity-effects in ligand-inducedChemical science · 2026Article
- Reactivity of a Sodium Anion with Alkenes: 1-Electron vs 2-Electron Reductions.Inorganic chemistry · 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
- Harnessing Organopotassium Reagents for Cross-Coupling with YPhos-Pd Catalysts: Opportunities, Applications, and Challenges.Journal of the American Chemical Society · 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
- Continuous flow synthesis enabling reaction discovery.Chemical science · 2024Review
- In Situ Quench Reactions of Enantioenriched Secondary Alkyllithium Reagents in Batch and Continuous Flow Using an I/Li-Exchange.Angewandte Chemie (International ed. in English) · 2023Article
- Article
- Sodium Isopropyl(trimethylsilyl)amide: A Stable and Highly Soluble Lithium Diisopropylamide Mimic.The Journal of organic chemistry · 2022Article
- Continuous Flow Preparation of Benzylic Sodium Organometallics.Angewandte Chemie (International ed. in English) · 2022Article
- Enhancing Metalating Efficiency of the Sodium Amide NaTMP in Arene Borylation Applications.Angewandte Chemie (International ed. in English) · 2022Article
- Synthesis of odorants in flow and their applications in perfumery.Beilstein journal of organic chemistry · 2022Review
- Ketone Enolization with Sodium Hexamethyldisilazide: Solvent- and Substrate-DependentJournal of the American Chemical Society · 2021Article
- Continuous Flow Acylation of (Hetero)aryllithiums with Polyfunctional N,N-Dimethylamides and Tetramethylurea in Toluene.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Reactions of Sodium Diisopropylamide: Liquid-Phase and Solid-Liquid Phase-Transfer Catalysis byJournal of the American Chemical Society · 2021Article
- (2-Ethylhexyl)sodium: A Hexane-Soluble Reagent for Br/Na-Exchanges and Directed Metalations in Continuous Flow.Angewandte Chemie (International ed. in English) · 2021Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
6 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
We report the on-demand generation of hexane-soluble (2-ethylhexyl)sodium (1) from 3-(chloromethyl)heptane (2) using a sodium-packed-bed reactor under continuous flow conditions. Thus, the resulting solution of 1 is free of elemental sodium and therefore suited for a range of synthetic applications. This new procedure avoids the storage of an alkylsodium and limits the handling of metallic sodium to a minimum. (2-Ethylhexyl)sodium (1) proved to be a very useful reagent and undergoes in-line Br/Na-exchanges as well as directed sodiations. The resulting arylsodium intermediates are subsequently trapped in batch with various electrophiles such as ketones, aldehydes, Weinreb-amides, imines, allyl bromides, disulfides and alkyl iodides. A reaction scale-up of the Br/Na-exchange using an in-line electrophile quench was also reported.
Indexed as
Identifiers
What OpenQuestion holds
Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.