Scholarlink

<p>Aryl <i>C</i>-glycosides are privileged scaffolds in drug discovery, biochemical research, and materials science. Established methods for their synthesis typically involve radical cross-coupling of saccharides. However, the glycosyl donors required in these methods encounter longstanding challenges, including instability and the need for prefunctionalization at the anomeric position. Herein, we report a highly efficient radical cross-coupling approach in which the native hydroxyl group on saccharides is activated in situ by a phosphorus reagent, enabling C − C bond formation with aryl iodides to afford a broad range of aryl <i>C</i>-glycosides. A combination of Zn and I<sub>2</sub> is developed for initiating the key <i>β</i>-scission step. Importantly, the glycosyl donors are bench-stable and readily available, addressing the issues associated with previous donors. Furthermore, this method offers an attractive strategy for the direct synthesis of drug-sugar conjugates and therapeutic agents. Mechanistic experiments and density functional theory (DFT) calculations provide strong support for the proposed reaction mechanism.</p>

错误：搜索内容不能为空，请输入英文关键词
错误：关键词超出字数限制，请精简
高级检索

Direct deoxygenative arylation of saccharides via phosphorus-assisted C−OH bond activation

  • 期刊论文

  • 出版模式：

    开放获取

  • 发表日期：

    2025年12月6日

查看全文
  • Xiang-Yu Ye,
  • Shiqing Huang,
  • Shuai Guo,
  • Guanjie Wang,
  • Wen-Xin Lv,
  • Yonggui Robin Chi

摘要

Aryl C-glycosides are privileged scaffolds in drug discovery, biochemical research, and materials science. Established methods for their synthesis typically involve radical cross-coupling of saccharides. However, the glycosyl donors required in these methods encounter longstanding challenges, including instability and the need for prefunctionalization at the anomeric position. Herein, we report a highly efficient radical cross-coupling approach in which the native hydroxyl group on saccharides is activated in situ by a phosphorus reagent, enabling C − C bond formation with aryl iodides to afford a broad range of aryl C-glycosides. A combination of Zn and I2 is developed for initiating the key β-scission step. Importantly, the glycosyl donors are bench-stable and readily available, addressing the issues associated with previous donors. Furthermore, this method offers an attractive strategy for the direct synthesis of drug-sugar conjugates and therapeutic agents. Mechanistic experiments and density functional theory (DFT) calculations provide strong support for the proposed reaction mechanism.