Scholarlink

<p>Minimizing side reactions is essential for achieving high yield and selectivity in organic synthesis, yet controlling overoxidation in direct benzylic C–H bond hydroxylation remains challenging. Here we show an electrochemical method for benzylic C–H hydroxylation using water as the oxygen source, in which overoxidation is suppressed by employing N-methyl-2-pyrrolidone as a co-solvent. The reaction proceeds without external oxidants, metal catalysts, or an inert atmosphere, using simple electrolytes. It is compatible with primary, secondary, and tertiary alkylarenes and exhibits good functional group tolerance. The method also enables isotope incorporation and is readily scalable, demonstrating practical synthetic utility. Mechanistic studies suggest that dual hydrogen-bonding interactions between the alcohol product and N-methyl-2-pyrrolidone may play a key role in suppressing overoxidation. Although the faradaic efficiency is moderate under the current conditions, this work provides a complementary strategy for selective benzylic C–H hydroxylation using water as a benign oxygen source.</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

Electrochemical Direct Benzylic C–H Hydroxylation with H2O Enabled by an Unusual Dual Hydrogen-bonding Interaction

  • 期刊论文

  • 出版模式：

    开放获取

  • 发表日期：

    2026年5月20日

查看全文
  • Shuaiyu Ji,
  • Wing-Yiu Yu,
  • Peng Yu

摘要

Minimizing side reactions is essential for achieving high yield and selectivity in organic synthesis, yet controlling overoxidation in direct benzylic C–H bond hydroxylation remains challenging. Here we show an electrochemical method for benzylic C–H hydroxylation using water as the oxygen source, in which overoxidation is suppressed by employing N-methyl-2-pyrrolidone as a co-solvent. The reaction proceeds without external oxidants, metal catalysts, or an inert atmosphere, using simple electrolytes. It is compatible with primary, secondary, and tertiary alkylarenes and exhibits good functional group tolerance. The method also enables isotope incorporation and is readily scalable, demonstrating practical synthetic utility. Mechanistic studies suggest that dual hydrogen-bonding interactions between the alcohol product and N-methyl-2-pyrrolidone may play a key role in suppressing overoxidation. Although the faradaic efficiency is moderate under the current conditions, this work provides a complementary strategy for selective benzylic C–H hydroxylation using water as a benign oxygen source.