Photosensitizer-free visible-light-mediated gold-catalyzed 1,2-difunctionalization of alkynes
Under visible-light irradiation, the gold-catalyzed intermolecular difunctionalization of alkynes with aryl diazonium salts in methanol affords a variety of α-aryl ketones in moderate to good yields. In contrast to previous reports on gold-catalyzed reactions that involve redox cycles, no external o...
Gespeichert in:
| Hauptverfasser: | , , , |
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| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
11 March 2016
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| In: |
Angewandte Chemie. International edition
Year: 2016, Jahrgang: 55, Heft: 15, Pages: 4808-4813 |
| ISSN: | 1521-3773 |
| DOI: | 10.1002/anie.201511487 |
| Online-Zugang: | Verlag, Volltext: http://dx.doi.org/10.1002/anie.201511487 Verlag, Volltext: http://onlinelibrary.wiley.com/doi/10.1002/anie.201511487/abstract 
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| Verfasserangaben: | Long Huang, Matthias Rudolph, Frank Rominger, and A. Stephen K. Hashmi |
MARC
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| 520 | |a Under visible-light irradiation, the gold-catalyzed intermolecular difunctionalization of alkynes with aryl diazonium salts in methanol affords a variety of α-aryl ketones in moderate to good yields. In contrast to previous reports on gold-catalyzed reactions that involve redox cycles, no external oxidants or photosensitizers are required. The reaction proceeds smoothly under mild reaction conditions and shows broad functional-group tolerance. Further applications of this method demonstrate the general applicability of the arylation of a vinyl gold intermediate instead of the commonly used protodemetalation step. This step provides facile access to functionalized products in one-pot processes. With a P,N-bidentate ligand, a stable aryl gold(III) species was obtained, which constitutes the first direct experimental evidence for the commonly postulated direct oxidative addition of an aryl diazonium salt to a pyridine phosphine gold(I) complex. | ||
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