Guo Xuqiang, Cui Xinwen, Lu Mingzhen, Zhou Qi-Lin, Xu Weiwei, Ye Mengchun
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, China.
Haihe Laboratory of Sustainable Chemical Transformations, Tianjin, China.
Nat Commun. 2025 May 15;16(1):4504. doi: 10.1038/s41467-025-59274-4.
Oxidation of alkenes with O 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.
用氧气和光激发的硝基芳烃氧化烯烃是合成富氧分子最具吸引力的有机化学转化反应之一。然而，已知的成果主要局限于烯烃的碳链缩短氧化和碳链保留氧化。鉴于构建更高的分子复杂性是现代合成的核心目标，烯烃的链增长氧化的发展将备受需求，但迄今为止仍然是一个难以实现的挑战。在此，我们报道了一种光激发的硝基芳烃介导的烯烃的高度区域选择性链增长氧化反应，该反应通过串联氧化裂解和偶极环加成实现，在简单温和的条件下，从容易获得的烯醇醚或苯乙烯及其衍生物中以高达92%的产率提供了多种具有合成用途的异恶唑烷。
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