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Direct asymmetric ruthenium-catalyzed reductive amination of alkyl-aryl ketones with ammonia and hydrogen

The asymmetric ruthenium-catalyzed reductive amination employing ammonia and hydrogen to primary amines is described. Here we demonstrate the capability of our catalyst to perform a chemo- and enantioselective process while using simple ammonia gas as a reagent, one of the most attractive and indust...

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Hauptverfasser: Gallardo-Donaire, Joan (VerfasserIn) , Hermsen, Marko (VerfasserIn) , Wysocki, Jędrzej (VerfasserIn) , Rominger, Frank (VerfasserIn) , Trapp, Oliver (VerfasserIn) , Hashmi, A. Stephen K. (VerfasserIn) , Comba, Peter (VerfasserIn) , Schaub, Thomas (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: 2018
In: Journal of the American Chemical Society
Year: 2017, Jahrgang: 140, Heft: 1, Pages: 355-361
ISSN:1520-5126
DOI:10.1021/jacs.7b10496
Online-Zugang:Verlag, Volltext: http://dx.doi.org/10.1021/jacs.7b10496
Verlag, Volltext: https://doi.org/10.1021/jacs.7b10496
Volltext
Verfasserangaben:Joan Gallardo-Donaire, Marko Hermsen, Jedrzej Wysocki, Martin Ernst, Frank Rominger, Oliver Trapp, A. Stephen K. Hashmi, Ansgar Schäfer, Peter Comba, and Thomas Schaub
Beschreibung
Zusammenfassung:The asymmetric ruthenium-catalyzed reductive amination employing ammonia and hydrogen to primary amines is described. Here we demonstrate the capability of our catalyst to perform a chemo- and enantioselective process while using simple ammonia gas as a reagent, one of the most attractive and industrially relevant nitrogen sources. The presence of a catalytic amount of ammonium iodide was essential for obtaining good yields and enantioselectivities. The mechanism of this reaction was investigated by DFT and we found a viable pathway that also explains the trend and magnitude of enantioselectivity through the halide series in good agreement with the experimental data. The in-depth investigation of substrate conformers during the reaction turned out to be crucial in obtaining an accurate prediction of the enantioselectivity. Furthermore, we report the crystallographic data of the chiral [Ru(I)H(CO)((S,S)-f-binaphane)(PPh3)] complex, which we identified as the most efficient catalyst in our investigation.
Beschreibung:Published: December 1, 2017
Gesehen am 13.06.2018
Beschreibung:Online Resource
ISSN:1520-5126
DOI:10.1021/jacs.7b10496

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