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<p>Oxidation of alkenes with O<sub>3</sub> and photoexcited nitroarenes represents one of the most attractive organic chemical transformations for the synthesis of oxygen-enriched molecules. However, known achievements are mainly limited to carbon chain-shortened oxidation and carbon chain-retained oxidation of alkenes. Given that constructing higher molecular complexity is the core goal of modern synthesis, the development of chain-elongated oxidation of alkenes would be in high demand but still remains an elusive challenge so far. Herein, we report a photoexcited nitroarene-enabled highly regioselective chain-elongated oxidation of alkenes via tandem oxidative cleavage and dipolar cycloaddition, providing a broad range of synthetically-useful isoxazolidines in up to 92% yield from readily available enol ethers or styrene and derivatives under simple and mild conditions.</p>

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Photoexcited nitroarene-enabled carbon chain-elongated oxidation of alkenes via tandem oxidative cleavage and dipolar cycloaddition

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2025年5月15日

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  • Xuqiang Guo,
  • Xinwen Cui,
  • Mingzhen Lu,
  • Qi-Lin Zhou,
  • Weiwei Xu,
  • Mengchun Ye

摘要

Oxidation of alkenes with O3 and photoexcited nitroarenes represents one of the most attractive organic chemical transformations for the synthesis of oxygen-enriched molecules. However, known achievements are mainly limited to carbon chain-shortened oxidation and carbon chain-retained oxidation of alkenes. Given that constructing higher molecular complexity is the core goal of modern synthesis, the development of chain-elongated oxidation of alkenes would be in high demand but still remains an elusive challenge so far. Herein, we report a photoexcited nitroarene-enabled highly regioselective chain-elongated oxidation of alkenes via tandem oxidative cleavage and dipolar cycloaddition, providing a broad range of synthetically-useful isoxazolidines in up to 92% yield from readily available enol ethers or styrene and derivatives under simple and mild conditions.