Oxidative gold catalysis meets photochemistry - synthesis of benzo(a)fluorenones from diynes
Diynes bearing one terminal and one triarylmethyl-substituted alkyne were converted into complex benzofluorenone derivatives via a one-pot process involving a gold-catalyzed step followed by a photocyclization/oxidation. In the first step an N-oxide was used to position-selectively generate an α-oxo...
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| Hauptverfasser: | , , , , |
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| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
14 November 2014
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| In: |
Advanced synthesis & catalysis
Year: 2014, Jahrgang: 356, Heft: 18, Pages: 3755-3760 |
| ISSN: | 1615-4169 |
| DOI: | 10.1002/adsc.201400969 |
| Online-Zugang: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/adsc.201400969 Verlag, lizenzpflichtig, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/adsc.201400969 
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| Verfasserangaben: | Pascal Nösel, Setareh Moghimi, Christoph Hendrich, Marten Haupt, Matthias Rudolph, Frank Rominger, and A. Stephen K. Hashmi |
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| 520 | |a Diynes bearing one terminal and one triarylmethyl-substituted alkyne were converted into complex benzofluorenone derivatives via a one-pot process involving a gold-catalyzed step followed by a photocyclization/oxidation. In the first step an N-oxide was used to position-selectively generate an α-oxo carbenoid at the terminal alkyne which after a regioselective 1,6-carbene transfer along the tethered tritylalkyne and a subsequent aryl 1,2-shift furnished tetraphenylethylene-like derivatives. These intermediates were successfully transformed to fluorenones via oxidative photocyclization. | ||
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