Dual gold catalysis: synthesis of fluorene derivatives from diynes
1,5-Diyne systems bearing one terminal and one benzyl- or allyl-substituted alkyne attached to an aromatic backbone were converted in the presence of a gold catalyst. In a dual gold-catalyzed process, gold vinylidenes are formed that selectively undergo formal CH insertion into the C(sp2)-H bond of...
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| Main Authors: | , , , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
2017
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| In: |
Advanced synthesis & catalysis
Year: 2016, Volume: 359, Issue: 2, Pages: 225-233 |
| ISSN: | 1615-4169 |
| DOI: | 10.1002/adsc.201600987 |
| Online Access: | Verlag, Volltext: http://dx.doi.org/10.1002/adsc.201600987 Verlag, Volltext: http://onlinelibrary.wiley.com/doi/10.1002/adsc.201600987/abstract 
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| Author Notes: | Janina Bucher, Thomas Wurm, Svenja Taschinski, Eleni Sachs, David Ascough, Matthias Rudolph, Frank Rominger, A. Stephen K. Hashmi |
| Summary: | 1,5-Diyne systems bearing one terminal and one benzyl- or allyl-substituted alkyne attached to an aromatic backbone were converted in the presence of a gold catalyst. In a dual gold-catalyzed process, gold vinylidenes are formed that selectively undergo formal CH insertion into the C(sp2)-H bond of the offered unsaturated systems. If H atoms are present in the propargylic position, a subsequent isomerization to the aromatic system takes place leading to 9H-fluorene and 11H-benzo[b]fluorene derivatives as final products. In the case of a quaternary carbon in the propargylic position no further aromatization is observed and 10H-benzo[b]fluorene derivatives are obtained in high yield. |
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| Item Description: | Online published: 8 December 2016 |
| Physical Description: | Online Resource |
| ISSN: | 1615-4169 |
| DOI: | 10.1002/adsc.201600987 |