1,6-carbene transfer: gold-catalyzed oxidative diyne cyclizations
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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| Hauptverfasser: | , , , , , |
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| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
September 19, 2013
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| In: |
Journal of the American Chemical Society
Year: 2013, Jahrgang: 135, Heft: 41, Pages: 15662-15666 |
| ISSN: | 1520-5126 |
| DOI: | 10.1021/ja4085385 |
| Online-Zugang: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1021/ja4085385
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| Verfasserangaben: | Pascal Nösel, Laura Nunes dos Santos Comprido, Tobias Lauterbach, Matthias Rudolph, Frank Rominger, and A. Stephen K. Hashmi |
| Zusammenfassung: | 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. |
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| Beschreibung: | Gesehen am 25.11.2021 |
| Beschreibung: | Online Resource |
| ISSN: | 1520-5126 |
| DOI: | 10.1021/ja4085385 |