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Gold catalysis: catalyst oxidation state dependent dichotomy in the cyclization of furan-yne systems with aromatic tethers

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Four different synthetic strategies led to a variety of furan-yne systems that contained an aryl system in the tether. Due to the short routes to these systems (four steps or less), a small library of substrates could easily be prepared. These were treated with AuCl3 or with the Gagosz’s catalyst Ph...

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Hauptverfasser: Hashmi, A. Stephen K. (VerfasserIn) , Hofmann, Julia (VerfasserIn) , Shi, Shuai (VerfasserIn) , Schütz, Alexander (VerfasserIn) , Rudolph, Matthias (VerfasserIn) , Lothschütz, Christian (VerfasserIn) , Wieteck, Marcel (VerfasserIn) , Bührle, Miriam (VerfasserIn) , Rominger, Frank (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: 2013
In: Chemistry - a European journal
Year: 2013, Jahrgang: 19, Heft: 1, Pages: 382-389
ISSN:1521-3765
DOI:10.1002/chem.201202004
Online-Zugang:Verlag, Volltext: http://dx.doi.org/10.1002/chem.201202004
Verlag, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201202004
Volltext
Verfasserangaben:A. Stephen K. Hashmi, Julia Hofmann, Shuai Shi, Alexander Schütz, Matthias Rudolph, Christian Lothschütz, Marcel Wieteck, Miriam Bührle, Michael Wölfle, and Frank Rominger
Beschreibung
Zusammenfassung:Four different synthetic strategies led to a variety of furan-yne systems that contained an aryl system in the tether. Due to the short routes to these systems (four steps or less), a small library of substrates could easily be prepared. These were treated with AuCl3 or with the Gagosz’s catalyst Ph3PAuNTf2 complex. The AuCl3-catalyzed reactions delivered highly substituted fluorene derivatives, a class of compounds of great importance as precursors for luminophores with extraordinary abilities. Conversely, a different mechanistic pathway was observed with the cationic gold(I) catalyst. In the latter case, a mechanistically interesting reaction cascade initiated a formal alkyne insertion into the furyl-sp3-C bond, which gave indene derivatives as the final products. This new reaction pathway depends on the aromatic moiety in the tether, which stabilizes a crucial cationic intermediate as a benzylic cation.
Beschreibung:Gesehen am 04.09.2018
Published online: November 13, 2012
Beschreibung:Online Resource
ISSN:1521-3765
DOI:10.1002/chem.201202004

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