Buchumschlag

Room-temperature hydrohydrazination of terminal alkynes catalyzed by saturated abnormal N-heterocyclic carbene-gold(I) complexes

Weitere Versionen anzeigen (1)

Abstract A number of saturated abnormal N-heterocyclic carbene (NHC) complexes of gold, in combination with KBArF4 as activator, were successfully applied in the chemoselective addition of hydrazine to alkynes. The reaction proceeds even at room temperature, which was not possible to date with gold...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Hauptverfasser: Manzano, Rubén (VerfasserIn) , Wurm, Thomas (VerfasserIn) , Rominger, Frank (VerfasserIn) , Hashmi, A. Stephen K. (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: April 25, 2014
In: Chemistry - a European journal
Year: 2014, Jahrgang: 20, Heft: 23, Pages: 6844-6848
ISSN:1521-3765
DOI:10.1002/chem.201402560
Online-Zugang:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/chem.201402560
Verlag, lizenzpflichtig, Volltext: https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/chem.201402560
Volltext
Verfasserangaben:Rubén Manzano, Thomas Wurm, Frank Rominger, and A. Stephen K. Hashmi
Beschreibung
Zusammenfassung:Abstract A number of saturated abnormal N-heterocyclic carbene (NHC) complexes of gold, in combination with KBArF4 as activator, were successfully applied in the chemoselective addition of hydrazine to alkynes. The reaction proceeds even at room temperature, which was not possible to date with gold catalysts. The reaction can be applied to a number of substituted arylalkynes. With alkylalkynes the yields are low. The saturated abnormal NHC ligands are resistant to isomerization to the saturated normal NHC coordination mode under basic reaction conditions. Under acidic conditions, a simple protonation at the nitrogen atom not neighboring the carbene center was observed and unambiguously characterized by an X-ray crystal-structure analysis. Computational studies confirm that such an isomerization would be highly exothermic, the observed kinetic stability probably results from the need to shift two protons in such a process.
Beschreibung:Gesehen am 13.08.2020
Beschreibung:Online Resource
ISSN:1521-3765
DOI:10.1002/chem.201402560

Ähnliche Einträge