The gold-catalyzed hydroarylation of alkynes with electron-rich heteroarenes: a kinetic investigation and new synthetic possibilities
The gold-catalyzed mono-hydroarylation and two-fold hydroarylation of alkynes with electron-rich heteroarenes was analyzed by a 1H NMR kinetic study. The obtained rate constants for the decreasing alkyne concentration provide information on the reactivity of this addition reaction. The examinations...
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| Main Authors: | , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
January 26, 2017
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| In: |
Advanced synthesis & catalysis
Year: 2017, Volume: 359, Issue: 4, Pages: 639-653 |
| ISSN: | 1615-4169 |
| DOI: | 10.1002/adsc.201600940 |
| Online Access: | Verlag, Volltext: http://dx.doi.org/10.1002/adsc.201600940 Verlag, Volltext: http://onlinelibrary.wiley.com/doi/10.1002/adsc.201600940/abstract Verlag, Volltext: http://onlinelibrary.wiley.com/doi/10.1002/adsc.201600940/epdf 
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| Author Notes: | Jasmin Schießl, Matthias Rudolph, A. Stephen K. Hashmi |
| Summary: | The gold-catalyzed mono-hydroarylation and two-fold hydroarylation of alkynes with electron-rich heteroarenes was analyzed by a 1H NMR kinetic study. The obtained rate constants for the decreasing alkyne concentration provide information on the reactivity of this addition reaction. The examinations show the orthogonal reactivity of gold and a proton for the two reaction steps. The first hydroarylation is exclusively promoted by gold(I), whereas the second step is premised on a proton which will be reversibly derived from the formation of σ,π-acetylide complexes from the terminal alkynes or by interaction with solvents. Based on kinetic data, it was possible to synthesize a large range of mono-adducts in moderate to good yields, furthermore the synthesis of hetero-di-adducts, bearing two different substituents, was explored. |
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| Item Description: | Gesehen am 22.08.2017 |
| Physical Description: | Online Resource |
| ISSN: | 1615-4169 |
| DOI: | 10.1002/adsc.201600940 |