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Copper(II)-catalyzed amination of aryl chlorides in aqueous ammonia

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 loadi...

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Hauptverfasser: Mello, Lucas S. (VerfasserIn) , Engel, Philipp D. (VerfasserIn) , Orecchia, Patrizio (VerfasserIn) , Bleher, Katharina (VerfasserIn) , Rominger, Frank (VerfasserIn) , Borate, Kailaskumar (VerfasserIn) , Goetz, Roland (VerfasserIn) , Deglmann, Peter (VerfasserIn) , Schäfer, Ansgar (VerfasserIn) , Winter, Christian (VerfasserIn) , Rack, Michael (VerfasserIn) , Comba, Peter (VerfasserIn) , Hashmi, A. Stephen K. (VerfasserIn) , Schaub, Thomas (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: December 5, 2024
In: Chemistry - a European journal
Year: 2024, Jahrgang: 30, Heft: 68, Pages: 1-10
ISSN:1521-3765
DOI:10.1002/chem.202403023
Online-Zugang:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/chem.202403023
Verlag, lizenzpflichtig, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.202403023
Volltext
Verfasserangaben: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
Beschreibung
Zusammenfassung: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.
Beschreibung:Online verfügbar: 22. August 2024
Gesehen am 01.04.2025
Beschreibung:Online Resource
ISSN:1521-3765
DOI:10.1002/chem.202403023

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