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Dual gold catalysis: synthesis of fluorene derivatives from diynes

1,5-Diyne systems bearing one terminal and one benzyl- or allyl-substituted alkyne attached to an aromatic backbone were converted in the presence of a gold catalyst. In a dual gold-catalyzed process, gold vinylidenes are formed that selectively undergo formal CH insertion into the C(sp2)-H bond of...

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Bibliographische Detailangaben
Hauptverfasser: Bucher, Janina (VerfasserIn) , Wurm, Thomas (VerfasserIn) , Taschinski, Svenja (VerfasserIn) , Rudolph, Matthias (VerfasserIn) , Rominger, Frank (VerfasserIn) , Hashmi, A. Stephen K. (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: 2017
In: Advanced synthesis & catalysis
Year: 2016, Jahrgang: 359, Heft: 2, Pages: 225-233
ISSN:1615-4169
DOI:10.1002/adsc.201600987
Online-Zugang:Verlag, Volltext: http://dx.doi.org/10.1002/adsc.201600987
Verlag, Volltext: http://onlinelibrary.wiley.com/doi/10.1002/adsc.201600987/abstract
Volltext
Verfasserangaben:Janina Bucher, Thomas Wurm, Svenja Taschinski, Eleni Sachs, David Ascough, Matthias Rudolph, Frank Rominger, A. Stephen K. Hashmi
Beschreibung
Zusammenfassung:1,5-Diyne systems bearing one terminal and one benzyl- or allyl-substituted alkyne attached to an aromatic backbone were converted in the presence of a gold catalyst. In a dual gold-catalyzed process, gold vinylidenes are formed that selectively undergo formal CH insertion into the C(sp2)-H bond of the offered unsaturated systems. If H atoms are present in the propargylic position, a subsequent isomerization to the aromatic system takes place leading to 9H-fluorene and 11H-benzo[b]fluorene derivatives as final products. In the case of a quaternary carbon in the propargylic position no further aromatization is observed and 10H-benzo[b]fluorene derivatives are obtained in high yield.
Beschreibung:Online published: 8 December 2016
Beschreibung:Online Resource
ISSN:1615-4169
DOI:10.1002/adsc.201600987

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