Oxyamination of Unactivated Alkenes with Electron-Rich Amines and Acids via a Catalytic Triiodide Intermediate.,Organic Letters

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Oxyamination of Unactivated Alkenes with Electron-Rich Amines and Acids via a Catalytic Triiodide Intermediate.
Organic Letters ( IF 4.9 ) Pub Date : 2020-01-13 , DOI: 10.1021/acs.orglett.9b04432
Fan Wu ₁ , Jeewani P Ariyarathna ₁ , Nur-E Alom ₁ , Navdeep Kaur ₁ , Wei Li ₁

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An aerobic catalytic oxidation process is described for the olefin oxyamination using acids and primary amines as the sources of O and N. Our mechanistic findings point to the formation of triiodide as a critical catalytic intermediate to account for the tolerance of electron-rich nucleophiles. This dual iodide and copper catalytic system is suitable for a formal [5+1] annulation process to access valuable lactam structures and highlighted by the synthesis of the pharmaceutical Zamifenacin.

中文翻译：

通过电子三碘化物中间体用富电子的胺和酸氧化未活化的烯烃。

描述了一种使用酸和伯胺作为O和N的源的烯烃氧化胺化的好氧催化氧化方法。我们的机理发现指出，三碘化物的形成是一种关键的催化中间体，说明了富电子亲核试剂的耐受性。这种双重碘化物和铜的催化体系适用于正式的[5 + 1]环化工艺，以获取有价值的内酰胺结构，并通过药物扎米芬星的合成得到突出显示。

更新日期：2020-01-14

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