A redox-neutral synthesis of ketones by coupling of alkenes and amides.,Nature Communications

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A redox-neutral synthesis of ketones by coupling of alkenes and amides.
Nature Communications ( IF 14.7 ) Pub Date : 2019-05-24 , DOI: 10.1038/s41467-019-10151-x
Jing Li ₁ , Rik Oost ₁ , Boris Maryasin _{1,

2} , Leticia González ₂ , Nuno Maulide ₁

Affiliation

The direct synthesis of ketones via carbon-carbon bond formation represents one of the most important challenges in organic synthesis. Hydroacylation of alkenes offers perhaps the most efficient and atom-economical approach for the preparation of ketones employing carbonyl compounds and alkenes as feedstocks. State-of-the-art hydroacylation is typically achieved by a transition metal-catalysed coupling of an aldehyde and an alkene but is plagued by competing decarbonylation, requiring the installation of directing groups in the aldehyde reactant. Herein, we present a method for the hydroacylation of alkenes employing amides in a metal-free regime, proceeding by a new mechanism and offering orthogonal reactivity to the conventional, metal-catalysed alternatives.

中文翻译：

通过烯烃和酰胺的偶联氧化还原中性合成酮。

通过碳-碳键形成直接合成酮是有机合成中最重要的挑战之一。烯烃的氢酰化可能为使用羰基化合物和烯烃作为原料制备酮提供了最有效和原子经济的方法。最先进的加氢酰化通常通过过渡金属催化的醛和烯烃的偶联来实现，但受到竞争性脱羰作用的困扰，需要在醛反应物中安装导向基团。在此，我们提出了一种在无金属状态下使用酰胺对烯烃进行加氢酰化的方法，该方法通过新的机制进行，并为传统的金属催化替代品提供正交反应性。

更新日期：2019-05-24

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