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Radical chain repair: The hydroalkylation of polysubstituted unactivated alkenes.
Science Advances ( IF 13.6 ) Pub Date : 2018-Jul-01 , DOI: 10.1126/sciadv.aat6031
Guillaume Povie 1 , Sankar Rao Suravarapu 1 , Martin Peter Bircher 1 , Melinda Meyer Mojzes 1 , Samuel Rieder 1 , Philippe Renaud 1
Affiliation  

The concept of repair is widely used by nature to heal molecules such as proteins, lipids, sugars, and DNA that are damaged by hydrogen atom abstraction resulting from oxidative stress. We show that this strategy, rather undocumented in the field of synthetic organic chemistry, can be used in a radical chain reaction to enable notoriously intractable transformations. By overcoming the radical chain inhibitor properties of substituted alkenes, the radical-mediated hydroalkylation of mono-, di-, tri-, and even tetrasubstituted unactivated olefins could be performed under mild conditions. With a remarkable functional group tolerance, this reaction provides a general coupling method for the derivatization of olefin-containing natural products.

中文翻译:

自由基链修复:多取代的未活化烯烃的加氢烷基化。

修复的概念在自然界已被广泛用于修复诸如蛋白质,脂质,糖和DNA之类的分子,这些分子被氧化应激导致的氢原子抽象所破坏。我们表明,这种策略在合成有机化学领域中未见报道,可用于自由基链反应中以实现众所周知的难处理的转化。通过克服取代烯烃的自由基链抑制剂性能,可以在温和条件下进行单,二,三,甚至四取代的未活化烯烃的自由基介导的加氢烷基化。该反应具有显着的官能团耐受性,为含烯烃的天然产物的衍生化提供了一种通用的偶联方法。
更新日期:2018-07-21
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