The reactivity of oxaziridines is significantly influenced by the substituents on the nitrogen atom. Despite extensive studies since their discovery by Emmons in 1956, research on the reactivity of N-aryl/heteroaryl oxaziridines remains limited. This limitation is likely due to the lack of efficient synthetic methods. In this study, a visible -light-induced photochemical strategy was developed to address this challenge. First, a series of stable biaryl-substituted N-heteroaryl oxaziridines were synthesized and isolated via the photochemical reaction of aryl/aryl diazoalkanes with nitrosoarenes. Further studies showed that some unstable N-aryl/heteroaryl oxaziridines, generated in-situ from the photochemical rearrangement of nitrones, show remarkable heteroatom transfer reactivities. These oxaziridines can act as both oxygen and nitrogen atom transfer reagents, depending on the nucleophiles involved. Moreover, the synthetic potential of this method was further highlighted through the successful modification of complex natural products and pharmaceutical derivatives. This study provides valuable insights into the synthesis and application of N-aryl/heteroaryl oxaziridines, thereby enhancing their utility in synthetic chemistry.

中文翻译：

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N-芳基/杂芳基恶氮环啶：从光化学合成到杂原子转移反应的反应性研究


恶氮环啶的反应性受氮原子上的取代基的显着影响。尽管自 1956 年 Emmons 发现 N-芳基/杂芳基恶氮啶以来进行了大量研究，但对 N-芳基/杂芳基恶氮啶的反应性的研究仍然有限。这种限制可能是由于缺乏有效的合成方法。在这项研究中，开发了一种可见光诱导的光化学策略来应对这一挑战。首先，通过芳基/芳基重氮烷烃与亚硝基噁芳烃的光化学反应，合成并分离了一系列稳定的联芳基取代的 N-杂芳基噁氮啶。进一步的研究表明，由硝基的光化学重排原位生成的一些不稳定的 N-芳基/杂芳基噁氮嗪表现出显着的杂原子转移反应性。这些恶氮环啶可以用作氧和氮原子转移试剂，具体取决于所涉及的亲核试剂。此外，通过对复杂天然产物和药物衍生物的成功改性，该方法的合成潜力进一步突出。本研究为 N-芳基/杂芳基噁氮啶的合成和应用提供了有价值的见解，从而提高了它们在合成化学中的实用性。