Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan.
J Org Chem. 2021 Mar 19;86(6):4699-4713. doi: 10.1021/acs.joc.1c00101. Epub 2021 Mar 9.
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.
酰亚胺是有机合成中用途广泛的构建模块。然而，氨基酸衍生的酰亚胺的合成具有一定难度，但需求很高。在此，我们公开了一种铜催化的磺酰胺（包括氨基酸和肽衍生物）与炔基苯并噁唑酮的 Csp-N 偶联反应，在温和的反应条件下，以广泛的官能团容忍度得到酰亚胺。富电子的联吡啶作为配体，乙醇作为溶剂，成功地进行了该反应。所得到的氨基酸衍生的酰亚胺作为构建块的有用性通过进一步衍生化得到独特的氨基酸衍生物得到了展示。还描述了一个用于阐明机理见解的对照实验。
