On the Gold-Catalyzed Intramolecular 7-exo-trig Hydroamination of Allenes

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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Veröffentlicht in:Advanced synthesis & catalysis 2013-05, Vol.355 (7), p.1383-1393
Hauptverfasser: Pflästerer, Daniel, Dolbundalchok, Praphasiri, Rafique, Shahid, Rudolph, Matthias, Rominger, Frank, Hashmi, A. Stephen K.
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Sprache:eng
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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.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201300154