Gold catalysis: catalyst oxidation state dependent dichotomy in the cyclization of furan-yne systems with aromatic tethers
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: | , , , , , , , , |
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| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
2013
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| 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 
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| Verfasserangaben: | A. Stephen K. Hashmi, Julia Hofmann, Shuai Shi, Alexander Schütz, Matthias Rudolph, Christian Lothschütz, Marcel Wieteck, Miriam Bührle, Michael Wölfle, and Frank Rominger |
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| 245 | 1 | 0 | |a Gold catalysis |b catalyst oxidation state dependent dichotomy in the cyclization of furan-yne systems with aromatic tethers |c A. Stephen K. Hashmi, Julia Hofmann, Shuai Shi, Alexander Schütz, Matthias Rudolph, Christian Lothschütz, Marcel Wieteck, Miriam Bührle, Michael Wölfle, and Frank Rominger |
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| 520 | |a 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. | ||
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