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

Sandro Cacchi, Giancarlo Fabrizi, Andrea Fochetti, Francesca Ghirga, Antonella Goggiamani, Antonia Iazzetti*

*Corresponding author

Research output: Contribution to journalArticle

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.
Original languageEnglish
Pages (from-to)527-532
Number of pages6
JournalORGANIC & BIOMOLECULAR CHEMISTRY
Volume17
DOIs
Publication statusPublished - 2019

Keywords

  • gold-catalysis
  • hydroamination
  • stereo and regio-selective reaction

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