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| Verfasst von: | Mello, Lucas S. [VerfasserIn]  |
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| | Engel, Philipp D. [VerfasserIn] |
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| | Orecchia, Patrizio [VerfasserIn] |
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| | Bleher, Katharina [VerfasserIn] |
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| | Rominger, Frank [VerfasserIn] |
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| | Borate, Kailaskumar [VerfasserIn] |
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| | Goetz, Roland [VerfasserIn] |
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| | Deglmann, Peter [VerfasserIn] |
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| | Schäfer, Ansgar [VerfasserIn] |
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| | Winter, Christian [VerfasserIn] |
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| | Rack, Michael [VerfasserIn] |
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| | Comba, Peter [VerfasserIn] |
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| | Hashmi, A. Stephen K. [VerfasserIn] |
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| | Schaub, Thomas [VerfasserIn] |
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| Titel: | Copper(II)-catalyzed amination of aryl chlorides in aqueous ammonia |
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| Verf.angabe: | Lucas S. Mello, Philipp D. Engel, Patrizio Orecchia, Katharina Bleher, Frank Rominger, Kailaskumar Borate, Roland Goetz, Peter Deglmann, Ansgar Schäfer, Christian Winter, Michael Rack, Peter Comba, A. Stephen K. Hashmi, and Thomas Schaub |
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| E-Jahr: | 2024 |
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| Jahr: | December 5, 2024 |
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| Umfang: | 10 S. |
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| Illustrationen: | Illustrationen |
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| Fussnoten: | Online verfügbar: 22. August 2024 ; Gesehen am 01.04.2025 |
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| Titel Quelle: | Enthalten in: Chemistry - a European journal |
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| Ort Quelle: | Weinheim : Wiley-VCH, 1995 |
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| Jahr Quelle: | 2024 |
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| Band/Heft Quelle: | 30(2024), 68, Artikel-ID e202403023, Seite 1-10 |
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| ISSN Quelle: | 1521-3765 |
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| Abstract: | Anilines are ubiquitous in bio-active compounds and their synthesis can be achieved via metal-catalyzed cross-coupling reactions involving aryl halides. We describe an unusual, yet simple, CuII-catalyzed system for the amination of aryl chlorides in pure aqueous ammonia with 2.5 mol % catalyst loading under non-inert conditions. Different from previous systems, the reaction proceeds even without an additional organic solvent. Copper(II) sulfate in combination with 4,7-dimethoxy-1,10-phenanthroline enabled the amination of several aryl chlorides containing electron-neutral, -donating and -withdrawing groups to the corresponding anilines with good to excellent yields. The upscaling potential of the procedure has been shown by the synthesis at 50 mmol scale. The reaction proceeds as one of the rare cases of a CuII-assisted coupling, in contrast to the typical CuI−CuIII intermediates postulated for most Ullmann-type coupling reactions. The copper(II) center allows for a nucleophilic substitution pathway, enabled by the deprotonation of coordinated ammonia. |
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| DOI: | doi:10.1002/chem.202403023 |
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| URL: | Bitte beachten Sie: Dies ist ein Bibliographieeintrag. Ein Volltextzugriff für Mitglieder der Universität besteht hier nur, falls für die entsprechende Zeitschrift/den entsprechenden Sammelband ein Abonnement besteht oder es sich um einen OpenAccess-Titel handelt.
Volltext: https://doi.org/10.1002/chem.202403023 |
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| | Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.202403023 |
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| | DOI: https://doi.org/10.1002/chem.202403023 |
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| Datenträger: | Online-Ressource |
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| Sprache: | eng |
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| Sach-SW: | Amination |
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| | Aniline synthesis |
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| | Copper catalysis |
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| | Cross-coupling |
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| | Nucleophilic aromatic substitution |
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| K10plus-PPN: | 1920966684 |
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| Verknüpfungen: | → Zeitschrift |
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Copper(II)-catalyzed amination of aryl chlorides in aqueous ammonia / Mello, Lucas S. [VerfasserIn]; December 5, 2024 (Online-Ressource)
