Direct Access to α-Aminosilanes Enabled by Visible-Light-Mediated Multicomponent Radical Cross-Coupling,Angewandte Chemie International Edition

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Direct Access to α-Aminosilanes Enabled by Visible-Light-Mediated Multicomponent Radical Cross-Coupling
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2021-08-25 , DOI: 10.1002/anie.202109252
Xiaoye Yu ₁ , Constantin G Daniliuc ₁ , Fatmah Ali Alasmary ₂ , Armido Studer _{1,

2}

Affiliation

α-Aminosilanes are an important class of organic compounds that show biological activity. In this communication, a new approach to α-aminosilanes that utilizes photoredox catalysis to enable three-component coupling of organo(tristrimethylsilyl)silanes with feedstock alkylamines and aldehydes is presented. A wide range of highly functionalized α-aminosilanes can be obtained in good yields under mild conditions. Both primary amines and secondary amines are compatible with this transformation. Moreover, optically pure α-aminosilanes are accessible by using chiral amines. Mechanistic studies indicate that reactions proceed through radical/radical cross-coupling of silyl radicals with α-amino alkyl radicals.

中文翻译：

通过可见光介导的多组分自由基交叉偶联直接获得α-氨基硅烷

α-氨基硅烷是一类具有生物活性的重要有机化合物。在本次交流中，提出了一种α-氨基硅烷的新方法，该方法利用光氧化还原催化使有机（三三甲基硅基）硅烷与原料烷基胺和醛进行三组分偶联。在温和条件下可以以良好的产率获得各种高度官能化的 α-氨基硅烷。伯胺和仲胺都适合这种转变。此外，通过使用手性胺可以获得光学纯的α-氨基硅烷。机理研究表明反应是通过甲硅烷基与α-氨基烷基的自由基/自由基交叉偶联进行的。

更新日期：2021-10-12

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