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Sequential gold-catalyzed carbene transfer/ring closure: oxidative cyclization of β-(2-Alkynylphenyl)-α,β-ynones to indenofuranones

β-(2-Alkynylphenyl)-α,β-ynones undergo a gold-catalyzed oxidative two-fold cyclization in the presence of N-oxides to give 1,3-disubstituted-8H-indeno[1,2-c]furan-8-ones in good yields. This cascade process is triggered by a selective oxygen transfer from an N-oxide onto the gold-activated alkynone...

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Bibliographische Detailangaben
Hauptverfasser: Rode, Navnath (VerfasserIn) , Adak, Tapas (VerfasserIn) , Rudolph, Matthias (VerfasserIn) , Rominger, Frank (VerfasserIn) , Hashmi, A. Stephen K. (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: November 14, 2018
In: Advanced synthesis & catalysis
Year: 2018, Jahrgang: 360, Heft: 24, Pages: 4790-4794
ISSN:1615-4169
DOI:10.1002/adsc.201801082
Online-Zugang:Resolving-System, Volltext: http://dx.doi.org/10.1002/adsc.201801082
Verlag, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/adsc.201801082
Volltext
Verfasserangaben:Navnath Rode, Fabio Marinelli, Antonio Arcadi, Tapas Adak, Matthias Rudolph, Frank Rominger, and A. Stephen K. Hashmi
Beschreibung
Zusammenfassung:β-(2-Alkynylphenyl)-α,β-ynones undergo a gold-catalyzed oxidative two-fold cyclization in the presence of N-oxides to give 1,3-disubstituted-8H-indeno[1,2-c]furan-8-ones in good yields. This cascade process is triggered by a selective oxygen transfer from an N-oxide onto the gold-activated alkynone to generate a α-dioxocarbene intermediate which, via carbene transfer across the remaining alkyne moiety and subsequent cyclization through nucleophilic attack by a carbonyl oxygen, achieves the construction of 1,3-disubstituted fused polycyclic furans.
Beschreibung:Gesehen am 05.02.2019
Beschreibung:Online Resource
ISSN:1615-4169
DOI:10.1002/adsc.201801082

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