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<p>Using water as a hydrogen or oxygen source in organic synthesis has enabled various reductive and oxidative transformations, but incorporation of both hydrogen and oxygen atoms into the same molecule, representing an atom-economic and environmentally benign process, has scarcely been explored. Here we report a hydrogenative oxidation strategy using water as both a source of H<sub>2</sub> and formal oxidant, enabling the direct synthesis of lactams from <i>N</i>-heteroarenes and thereby eliminating the need for additional reductants and oxidants and minimizing waste generation. The reaction can be initiated either under low H<sub>2</sub> pressure or with a catalytic amount of H<sub>2</sub>, leading to the efficient transformation of various <i>N</i>-heteroarenes into lactams in excellent yield thanks to an in situ-generated, piperidine-based, ruthenium pincer complex that balances the hydrogenation and dehydrogenation processes. This study will promote the design of other hydrogenative oxidation reactions using water.</p><p></p>

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A hydrogenative oxidation strategy for the single-step synthesis of lactams from N-heteroarenes using water

  • 期刊论文

  • 发表日期：

    2025年1月20日

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  • Yaoyu Liang,
  • Jie Luo,
  • Cai You,
  • Yael Diskin-Posner,
  • David Milstein

摘要

Using water as a hydrogen or oxygen source in organic synthesis has enabled various reductive and oxidative transformations, but incorporation of both hydrogen and oxygen atoms into the same molecule, representing an atom-economic and environmentally benign process, has scarcely been explored. Here we report a hydrogenative oxidation strategy using water as both a source of H2 and formal oxidant, enabling the direct synthesis of lactams from N-heteroarenes and thereby eliminating the need for additional reductants and oxidants and minimizing waste generation. The reaction can be initiated either under low H2 pressure or with a catalytic amount of H2, leading to the efficient transformation of various N-heteroarenes into lactams in excellent yield thanks to an in situ-generated, piperidine-based, ruthenium pincer complex that balances the hydrogenation and dehydrogenation processes. This study will promote the design of other hydrogenative oxidation reactions using water.