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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| Main Authors: | , , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
November 14, 2018
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| In: |
Advanced synthesis & catalysis
Year: 2018, Volume: 360, Issue: 24, Pages: 4790-4794 |
| ISSN: | 1615-4169 |
| DOI: | 10.1002/adsc.201801082 |
| Online Access: | Resolving-System, Volltext: http://dx.doi.org/10.1002/adsc.201801082 Verlag, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/adsc.201801082 
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| Author Notes: | Navnath Rode, Fabio Marinelli, Antonio Arcadi, Tapas Adak, Matthias Rudolph, Frank Rominger, and A. Stephen K. Hashmi |
| Summary: | 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. |
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| Item Description: | Gesehen am 05.02.2019 |
| Physical Description: | Online Resource |
| ISSN: | 1615-4169 |
| DOI: | 10.1002/adsc.201801082 |