Cyclization of gold acetylides: synthesis of vinyl sulfonates via gold vinylidene complexes
Differently substituted terminal alkynes that bear sulfonate leaving groups at an appropriate distance were converted in the presence of a propynyl gold(I) precatalyst. After initial formation of a gold acetylide, a cyclization takes place at the β-carbon atom of this species. Mechanistic studies su...
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| Main Authors: | , , , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
March 5, 2014
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| In: |
Angewandte Chemie. International edition
Year: 2014, Volume: 53, Issue: 15, Pages: 3854-3858 |
| ISSN: | 1521-3773 |
| DOI: | 10.1002/anie.201310280 |
| Online Access: | Resolving-System, lizenzpflichtig, Volltext: https://doi.org/10.1002/anie.201310280 Verlag, lizenzpflichtig, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201310280 
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| Author Notes: | Janina Bucher, Thomas Wurm, Kumara Swamy Nalivela, Matthias Rudolph, Frank Rominger, and A. Stephen K. Hashmi |
| Summary: | Differently substituted terminal alkynes that bear sulfonate leaving groups at an appropriate distance were converted in the presence of a propynyl gold(I) precatalyst. After initial formation of a gold acetylide, a cyclization takes place at the β-carbon atom of this species. Mechanistic studies support a mechanism that is related to that of dual gold-catalyzed reactions, but for the new substrates, only one gold atom is needed for substrate activation. After formation of a gold vinylidene complex, which forms a tight contact ion pair with the sulfonate leaving group, recombination of the two parts delivers vinyl sulfonates, which are valuable targets that can serve as precursors for cross-coupling reactions, for example. |
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| Item Description: | Gesehen am 29.07.2020 |
| Physical Description: | Online Resource |
| ISSN: | 1521-3773 |
| DOI: | 10.1002/anie.201310280 |