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1,6-carbene transfer: gold-catalyzed oxidative diyne cyclizations

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In the presence of a gold catalyst an unprecedented oxidative cyclization of diynes takes place. The reaction cascade is initiated by an oxygen transfer from a N-oxide onto a gold-activated alkyne. The formed α-oxo carbene is transferred across the second alkyne yielding a stabilized vinyl carbene/c...

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Bibliographic Details
Main Authors: Nösel, Pascal (Author) , Nunes dos Santos Comprido, Laura (Author) , Lauterbach, Tobias (Author) , Rudolph, Matthias (Author) , Rominger, Frank (Author) , Hashmi, A. Stephen K. (Author)
Format: Article (Journal)
Language:English
Published: September 19, 2013
In: Journal of the American Chemical Society
Year: 2013, Volume: 135, Issue: 41, Pages: 15662-15666
ISSN:1520-5126
DOI:10.1021/ja4085385
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1021/ja4085385
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Author Notes:Pascal Nösel, Laura Nunes dos Santos Comprido, Tobias Lauterbach, Matthias Rudolph, Frank Rominger, and A. Stephen K. Hashmi
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Summary:In the presence of a gold catalyst an unprecedented oxidative cyclization of diynes takes place. The reaction cascade is initiated by an oxygen transfer from a N-oxide onto a gold-activated alkyne. The formed α-oxo carbene is transferred across the second alkyne yielding a stabilized vinyl carbene/cation. Alkyl migration or sp3-CH insertion then terminates the catalytic cycle by formation of highly substituted functionalized indenones. A 1,6-carbene shift could be supported by the oxidation of the vinyl carbene. This protocol represents an attractive alternative to procedures which are based on the metal-catalyzed decomposition of hazardous, not easily accessible, diazo compounds.
Item Description:Gesehen am 25.11.2021
Physical Description:Online Resource
ISSN:1520-5126
DOI:10.1021/ja4085385

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