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首页> 外文期刊>Chemistry: A European journal >Synthetic Diversity from a Versatile and Radical Nitrating Reagent
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Synthetic Diversity from a Versatile and Radical Nitrating Reagent

机译：来自多功能和自由基氮化试剂的合成多样性

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摘要

We leverage the slow liberation of nitrogen dioxide from a newly discovered, inexpensive succinimide-derived reagent to allow for the C-H diversification of alkenes and alkynes. Beyond furnishing a library of aryl b-nitroalkenes, this reagent provides unparalleled access to b-nitrohydrins and b-nitroethers. Detailed mechanistic studies strongly suggest that a mesolytic N-N bond fragmentation liberates a nitryl radical. Using in situ photo-sensitized, electron paramagnetic resonance spectroscopy, we observed direct evidence of a nitryl radical in solution by nitrone spintrapping. To further exhibit versatility of N-nitrosuccinimide under photoredox conditions, the late-stage diversification of an extensive number of C-H partners to prepare isoxazolines and isoxazoles is presented. This approach allows for the formation of an in situ nitrile oxide from a ketone partner, the presence of which is detected by the formation of the corresponding furoxan when conducted in the absence of a dipolarophile. This 1,3-dipolar cycloaddition with nitrile oxides and alkenes or alkynes proceeds in a single-operational step using a mild, regioselective, and general protocol with broad chemoselectivity.
机译：我们利用新发现的，廉价的琥珀酰亚胺衍生的试剂的氮氧化物缓慢释放，以允许烯烃和炔烃的C-H多样化。除了装备芳基B-NITROALKENES文库，该试剂可提供对B-硝基氢胺和B-硝基乙烯的无与伦比的进入。具体的机制研究强烈表明，培霉N-N键碎裂释放出一种Nitryl基团。使用原位照片敏化，电子顺磁共振光谱，我们观察了通过硝基闪烁的溶液中的NitryL激进的直接证据。为了进一步在光毒毒剂条件下表现出N-亚硝琥珀酰亚胺的多功能性，提出了广泛数量的C-H合作伙伴的后期多样化以制备异恶唑啉和异恶唑。该方法允许从酮伴中形成原位腈氧化物，其存在通过在不存在二极管的情况下形成相应的呋喃丹来检测。该1,3-偶极环加料用丁腈氧化物和烯烃或炔烃在一次运行步骤中使用轻度，区域选择性和具有宽化学选择性的一般方案进行。

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  • 来源
    《Chemistry: A European journal》 |2019年第56期|共11页
  • 作者

    Kun Zhang; Benson Jelier; Alessandro Passera; Gunnar Jeschke; Dmitry Katayev;

  • 作者单位

    Department of Chemistry and Applied Biosciences Swiss Federal Institute of Technology ETH Zerich Vladimir-Prelog-Weg 2 8093 Zerich (Switzerland);

    Department of Chemistry and Applied Biosciences Swiss Federal Institute of Technology ETH Zerich Vladimir-Prelog-Weg 2 8093 Zerich (Switzerland);

    Department of Chemistry and Applied Biosciences Swiss Federal Institute of Technology ETH Zerich Vladimir-Prelog-Weg 2 8093 Zerich (Switzerland);

    Department of Chemistry and Applied Biosciences Swiss Federal Institute of Technology ETH Zerich Vladimir-Prelog-Weg 2 8093 Zerich (Switzerland);

    Department of Chemistry and Applied Biosciences Swiss Federal Institute of Technology ETH Zerich Vladimir-Prelog-Weg 2 8093 Zerich (Switzerland);

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  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 应用化学;
  • 关键词

    alkenes; C-H nitration; photoredox; radicals; reaction mechanisms;

    机译：alkenes;c-h硝化;photoreox;自由基;反应机制;

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