Anti-Markovnikov Hydroamination of Unactivated Alkenes with Primary Alkyl Amines,Journal of the American Chemical Society

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Anti-Markovnikov Hydroamination of Unactivated Alkenes with Primary Alkyl Amines
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2019-10-11 , DOI: 10.1021/jacs.9b08746
David C Miller ₁ , Jacob M Ganley ₁ , Andrew J Musacchio ₁ , Trevor C Sherwood ₂ , William R Ewing ₂ , Robert R Knowles ₁

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We report here a photocatalytic method for the intermolecular anti-Markovnikov hydroamination of unactivated olefins with primary alkyl amines to selectively furnish secondary amine products. These reactions proceed through aminium radical cation (ARC) intermediates and occur at room temperature under visible light irradiation in the presence of an iridium-based photocatalyst and an aryl thiol hydrogen atom donor. Despite the presence of excess olefin, high selectivities are observed for secondary over tertiary amine products, even though the secondary amines are estab-lished substrates for ARC-based olefin amination under similar conditions.

中文翻译：

未活化烯烃与伯烷基胺的反马尔科夫尼科夫加氢胺化

我们在这里报告了一种光催化方法，用于未活化烯烃与伯烷基胺的分子间抗马尔科夫尼科夫加氢胺化，以选择性地提供仲胺产物。这些反应通过胺自由基阳离子 (ARC) 中间体进行，并在铱基光催化剂和芳基硫醇氢原子供体的存在下，在室温下在可见光照射下发生。尽管存在过量烯烃，但观察到仲胺产物的选择性高于叔胺产物，即使仲胺是类似条件下基于 ARC 的烯烃胺化的既定底物。

更新日期：2019-10-11

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