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Oxidative gold catalysis meets photochemistry - synthesis of benzo(a)fluorenones from diynes

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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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Bibliographic Details
Main Authors: Nösel, Pascal (Author) , Hendrich, Christoph (Author) , Rudolph, Matthias (Author) , Rominger, Frank (Author) , Hashmi, A. Stephen K. (Author)
Format: Article (Journal)
Language:English
Published: 14 November 2014
In: Advanced synthesis & catalysis
Year: 2014, Volume: 356, Issue: 18, Pages: 3755-3760
ISSN:1615-4169
DOI:10.1002/adsc.201400969
Online Access: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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Author Notes:Pascal Nösel, Setareh Moghimi, Christoph Hendrich, Marten Haupt, Matthias Rudolph, Frank Rominger, and A. Stephen K. Hashmi
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Summary: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.
Item Description:Im Titel ist der Buchstabe "a" in eckigen Klammern
Gesehen am 29.10.2020
Physical Description:Online Resource
ISSN:1615-4169
DOI:10.1002/adsc.201400969

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