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  5. Stereo- and regioselective gold(I)-catalyzed hydroamination of 2-(arylethynyl)pyridines with anilines

Stereo- and regioselective gold(I)-catalyzed hydroamination of 2-(arylethynyl)pyridines with anilines

Author(s)
Fochetti, Andrea  
Fabrizi, Giancarlo
Iazzetti, Antonia
Goggiamani, Antonella
Ghirga, Francesca
more
Date Issued
2019
Type
article
Volume
17
Start Page
527
End Page
532
DOI
10.1039/c8ob02356e
Journal
ORGANIC & BIOMOLECULAR CHEMISTRY  
Abstract
The gold-catalyzed hydroamination of 2-(arylethynyl)pyridines with anilines affords stereoselectively Z-enamine products with excellent regioselectivity. The reaction proceeds with moderate to excellent yields and accommodates a diverse range of functional groups on alkynes (ether, bromo, trifluoromethyl, acetyl, and carbomethoxy) and anilines (ether, bromo, chloro, and carbethoxy). The stereochemistry of the obtained enamines is complementary to that reported in previous studies. A plausible explanation for the observed selectivity was attained by means of NMR experiments.
Handle
http://hdl.handle.net/2067/50940
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