Au(I)-Catalyzed Intramolecular Hydroamination of the Fluorinated N′-Aryl-N-Propargyl Amidines: Mild Conditions for the Synthesis of 2-Fluoroalkyl Imidazole Derivatives

Au(I)-Catalyzed Intramolecular Hydroamination of the Fluorinated N′-Aryl-N-Propargyl Amidines: Mild Conditions for the Synthesis of 2-Fluoroalkyl Imidazole Derivatives

The gold(I)-catalyzed synthesis of 2-fluoroalkyl imidazole derivatives was developed. Catalyzed by gold(I), propargyl amidines underwent a 5-exo-dig cyclization to afford 2-fluoroalkyl-5-methyl imidazoles. Also, 2-fluoroalkyl imidazole-5-carbaldehydes were obtained in the presence of NIS. A mechanis...

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Veröffentlicht in:Organic letters 2012-02, Vol.14 (4), p.1130-1133
Hauptverfasser: Li, Shan, Li, Zhengke, Yuan, Yafen, Peng, Dongjie, Li, Yajun, Zhang, Lisi, Wu, Yongming
Format: Artikel
Sprache:eng
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Zusammenfassung:The gold(I)-catalyzed synthesis of 2-fluoroalkyl imidazole derivatives was developed. Catalyzed by gold(I), propargyl amidines underwent a 5-exo-dig cyclization to afford 2-fluoroalkyl-5-methyl imidazoles. Also, 2-fluoroalkyl imidazole-5-carbaldehydes were obtained in the presence of NIS. A mechanism investigation manifested the probable process and the carbonyl oxygen derived from O2.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol3000525