ArticleAngewandte Chemie (International ed. in English)2022
Continuous Flow Preparation of Benzylic Sodium Organometallics.
Article in Angewandte Chemie (International ed. in English), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
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Who cites it
17 citing papers in PubMed, 47 citations in OpenAlex.
- Ligand- and alkali metal identity-effects in ligand-inducedChemical science · 2026Article
- Base-Promoted Benzylic C-H Amination Reactions Across a Wide pKa Spectrum Enabled by 2-Halobenzofuran and -Indole Oxidants.Journal of the American Chemical Society · 2026Article
- Deprotonative Single-Electron Oxidation as a General and Controllably Selective Platform for Benzylic C-H Functionalization.Journal of the American Chemical Society · 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
- Hydroalkylation of unactivated olefins with C(spScience advances · 2024Article
- Direct Benzylic C-H Etherification Enabled by Base-Promoted Halogen Transfer.Angewandte Chemie (International ed. in English) · 2024Article
- The Application of Flow Chemistry for the Synthesis of Alkyl Sodium Compounds and Their Transformations with Weinreb Amides and Carboxylic Acids.Organic letters · 2024Article
- Potassium Hexamethyldisilazide (KHMDS): Solvent-Dependent Solution Structures.Journal of the American Chemical Society · 2024Article
- Carbon-Nitrogen Bond Formation Using Sodium Hexamethyldisilazide: Solvent-Dependent Reactivities and Mechanisms.Journal of the American Chemical Society · 2023Article
- Li vs Na: Divergent Reaction Patterns between Organolithium and Organosodium Complexes and Ligand-Catalyzed Ketone/Aldehyde Methylenation.Journal of the American Chemical Society · 2023Article
- 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
- Continuous Flow Preparation of Benzylic Sodium Organometallics.Angewandte Chemie (International ed. in English) · 2022Article
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
We report a lateral sodiation of alkyl(hetero)arenes using on-demand generated hexane-soluble (2-ethylhexyl)sodium (1) in the presence of TMEDA. (2-Ethylhexyl)sodium (1) is prepared via a sodium packed-bed reactor and used for metalations at ambient temperature in batch as well as in continuous flow. The resulting benzylic sodium species are subsequently trapped with various electrophiles including carbonyl compounds, epoxides, oxetane, allyl/benzyl chlorides, alkyl halides and alkyl tosylates. Wurtz-type couplings with secondary alkyl halides and tosylates proceed under complete inversion of stereochemistry. Furthermore, the utility of this lateral sodiation is demonstrated in the synthesis of pharmaceutical relevant compounds. Thus, fingolimod is prepared from p-xylene applying the lateral sodiation twice. In addition, 7-fold isotopically labeled salmeterol-d
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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.