Ligand-Enabled Copper-Catalyzed <i>N</i>-Alkynylation of Sulfonamide with Alkynyl Benziodoxolone: Synthesis of Amino Acid-Derived Ynamide

DOI Web Site 被引用文献3件 参考文献92件
  • Ryogo Takai
    Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan
  • Daisuke Shimbo
    Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan
  • Norihiro Tada
    Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan
  • Akichika Itoh
    Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan

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説明

Ynamides are versatile building blocks in organic synthesis. However, the synthesis of amino acid-derived ynamides is difficult but in high demand. Herein, we disclose the copper-catalyzed Csp-N coupling of sulfonamide, including amino acid and peptide derivatives, to give ynamides by using alkynyl benziodoxolones with broad functional group tolerance under mild reaction conditions. The electron-rich bipyridine as a ligand and ethanol as solvent were used for the success of this reaction. The usefulness of the obtained amino acid-derived ynamide as building block was showcased by further derivatization to unique amino acid derivatives. A control experiment to elucidate the mechanistic insight was also described.

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