Gold-catalyzed dimerization of Diarylalkynes: direct access to Azulenes
We have developed a simple gold-catalyzed procedure for the synthesis of substituted and modifiable azulenes. The azulenes are formed either by the dimerization of push-pull diarylalkynes bearing a fluorine atom in ortho or para position or by the dimerization of a symmetric electron-rich diarylalky...
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| Main Authors: | , , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
September 24, 2018
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| In: |
Angewandte Chemie. International edition
Year: 2018, Volume: 57, Issue: 39, Pages: 12966-12970 |
| ISSN: | 1521-3773 |
| DOI: | 10.1002/anie.201805918 |
| Online Access: | Resolving-System, Volltext: http://dx.doi.org/10.1002/anie.201805918 Verlag, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201805918 
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| Author Notes: | Vanessa Claus, Michael Schukin, Siegfried Harrer, Matthias Rudolph, Frank Rominger, Abdullah M. Asiri, Jin Xie, and A. Stephen K. Hashmi |
| Summary: | We have developed a simple gold-catalyzed procedure for the synthesis of substituted and modifiable azulenes. The azulenes are formed either by the dimerization of push-pull diarylalkynes bearing a fluorine atom in ortho or para position or by the dimerization of a symmetric electron-rich diarylalkyne. In the presence of a cationic gold catalyst, the two alkynes can form a highly reactive vinyl cation. Trapping of this high-energy intermediate by an appropriate aryl unit then delivers substituted azulenes in a single step and in a perfect atom economy. |
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| Item Description: | Gesehen am 11.12.2018 |
| Physical Description: | Online Resource |
| ISSN: | 1521-3773 |
| DOI: | 10.1002/anie.201805918 |