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<p>The development of sustainable and efficient synthetic methodologies for high-valued chemicals from renewable resources is one of the principal aims of chemical industries. Herein, we document the combination of photocatalytic PCET and SCS-enabled direct C-H benzylation of <i>N</i>-heteroarenes with benzaldehydes as the benzyl sources. A variety of benzylated <i>N</i>-heteroarenes was obtained in moderate to excellent yields at room temperature under metal-, oxidant-free and mild conditions in continuous-flow mode. Mechanistic studies indicated that this benzylation proceeded via PCET activation of benzaldehydes to yield ketyl radicals, the addition of the ketyl radicals to <i>N</i>-heteroarenes to form C-C(OH) bonds, the SCS cleavage to produce benzylic radical and HAT process to deliver the benzylated products.</p>

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Combination of photocatalytic proton-coupled electron transfer and spin-center shift: direct C-H benzylation of N-heteroarenes with benzaldehydes in continuous-flow

  • 期刊论文

  • 发表日期：

    2025年2月24日

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  • Jia-Cheng Hou,
  • Jun Jiang,
  • Hui Dai,
  • Jia-Sheng Wang,
  • Ting Li,
  • Xiang Chen,
  • Wei-Min He

摘要

The development of sustainable and efficient synthetic methodologies for high-valued chemicals from renewable resources is one of the principal aims of chemical industries. Herein, we document the combination of photocatalytic PCET and SCS-enabled direct C-H benzylation of N-heteroarenes with benzaldehydes as the benzyl sources. A variety of benzylated N-heteroarenes was obtained in moderate to excellent yields at room temperature under metal-, oxidant-free and mild conditions in continuous-flow mode. Mechanistic studies indicated that this benzylation proceeded via PCET activation of benzaldehydes to yield ketyl radicals, the addition of the ketyl radicals to N-heteroarenes to form C-C(OH) bonds, the SCS cleavage to produce benzylic radical and HAT process to deliver the benzylated products.