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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...

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Bibliographic Details
Main Authors: Huang, Long (Author) , Rudolph, Matthias (Author) , Rominger, Frank (Author) , Hashmi, A. Stephen K. (Author)
Format: Article (Journal)
Language:English
Published: 11 March 2016
In: Angewandte Chemie. International edition
Year: 2016, Volume: 55, Issue: 15, Pages: 4808-4813
ISSN:1521-3773
DOI:10.1002/anie.201511487
Online Access: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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Author Notes:Long Huang, Matthias Rudolph, Frank Rominger, and A. Stephen K. Hashmi
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Summary: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.
Item Description:Gesehen am 29.09.2017
Physical Description:Online Resource
ISSN:1521-3773
DOI:10.1002/anie.201511487

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