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Gold(I)-Catalyzed Aminohalogenation of Fluorinated N′-Aryl-N-Propargyl Amidines for the Synthesis of Imidazole Derivatives under Mild Conditions

Authors

  • Dr Shan Li,

    1. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, 345 Lingling Road, Shanghai 200032 (P. R. China), Fax: (+86) 021-54925190
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  • Zhengke Li,

    1. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, 345 Lingling Road, Shanghai 200032 (P. R. China), Fax: (+86) 021-54925190
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  • Yafen Yuan,

    1. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, 345 Lingling Road, Shanghai 200032 (P. R. China), Fax: (+86) 021-54925190
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  • Yajun Li,

    1. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, 345 Lingling Road, Shanghai 200032 (P. R. China), Fax: (+86) 021-54925190
    2. School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, 1037 Luoyu Road, Wuhan, Hubei, 430074 (P. R. China)
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  • Lisi Zhang,

    1. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, 345 Lingling Road, Shanghai 200032 (P. R. China), Fax: (+86) 021-54925190
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  • Prof. Dr. Yongming Wu

    Corresponding author
    1. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, 345 Lingling Road, Shanghai 200032 (P. R. China), Fax: (+86) 021-54925190
    • Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, 345 Lingling Road, Shanghai 200032 (P. R. China), Fax: (+86) 021-54925190
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Abstract

A procedure for the synthesis of fluorinated imidazole derivatives from propargyl amidines has been developed. Under gold(I) catalysis, propargyl amidines were converted into 5-fluoromethyl imidazoles in the presence of Selectfluor through a cascade cyclization/fluorination process. In contrast, imidazole-5-carbaldehydes were obtained in high yields when N-iodosuccinimide (NIS) was used as the halogenating reagent. The polarity of the solvent and light had significant impact on the formation of the carbaldehydes. These transformations showed excellent functional-group tolerance. An unfluorinated substrate with an electron-withdrawing group also underwent aminohalogenation to give the corresponding product in good yield. Mechanistic investigation revealed the general pathways of these transformations.

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