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On the gold-catalyzed intramolecular 7-exo-trig hydroamination of allenes

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Aniline derivatives with allene side tethers were tested as substrates for a gold-catalyzed 7-exo-trig hydroamination reaction. The nucleophilicity of the aniline derivatives plays an important role for the outcome of the reaction. While electron-deficient protecting groups at the nitrogen led to co...

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Hauptverfasser: Pflästerer, Daniel (VerfasserIn) , Dolbundalchok, Praphasiri (VerfasserIn) , Rafique, Shahid (VerfasserIn) , Rudolph, Matthias (VerfasserIn) , Rominger, Frank (VerfasserIn) , Hashmi, A. Stephen K. (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: April 30, 2013
In: Advanced synthesis & catalysis
Year: 2013, Jahrgang: 355, Heft: 7, Pages: 1383-1393
ISSN:1615-4169
DOI:10.1002/adsc.201300154
Online-Zugang:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/adsc.201300154
Verlag, lizenzpflichtig, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/adsc.201300154
Volltext
Verfasserangaben:Daniel Pflästerer, Praphasiri Dolbundalchok, Shahid Rafique, Matthias Rudolph, Frank Rominger, and A. Stephen K. Hashmi
Beschreibung
Zusammenfassung:Aniline derivatives with allene side tethers were tested as substrates for a gold-catalyzed 7-exo-trig hydroamination reaction. The nucleophilicity of the aniline derivatives plays an important role for the outcome of the reaction. While electron-deficient protecting groups at the nitrogen led to competing pathways like hydroarylation or an allene to diene isomerization, clean formation of the desired benzoxazepines was obtained with unprotected aniline derivatives.
Beschreibung:Gesehen am 20.01.2022
Beschreibung:Online Resource
ISSN:1615-4169
DOI:10.1002/adsc.201300154

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