N. D. Zelinsky Institute of Organic Chemistry , Leninsky prosp. 47, 119991 Moscow, Russian Federation.
Org Lett. 2018 Feb 2;20(3):840-843. doi: 10.1021/acs.orglett.7b03987. Epub 2018 Jan 22.
A method for the addition of fluorinated groups to nitrones using an iridium photocatalyst and ascorbic acid as a stoichiometric reducing agent is described. The reaction proceeds through the generation of fluorinated radicals by single-electron reduction of fluorinated alkyl iodides with an iridium complex mediated by visible light. Besides perfluorinated reagents, partially fluorinated alkyl iodides can also be effectively used leading to the products, which cannot be obtained by conventional nucleophilic addition reactions. The resulting hydroxylamines can be readily converted to valuable fluorinated amines by reduction with zinc.
描述了一种使用铱光催化剂和抗坏血酸作为化学计量还原剂将氟基团添加到硝酮中的方法。该反应通过铱配合物介导的可见光下的单电子还原将氟化烷基碘化物还原为氟代自由基来进行。除了全氟试剂外，部分氟化烷基碘化物也可以有效地使用，从而得到通过常规亲核加成反应无法获得的产物。所得的羟胺可以很容易地通过锌还原转化为有价值的氟代胺。
