Rode Katharina, Ramadas Narasimhamurthy Poorva, Rieger Rene, Krätzschmar Felix, Breder Alexander
Institut für Organische und Biomolekulare Chemie Universität Göttingen Tammannstr. 2 37077 Göttingen Germany.
Faculty of Chemistry and Pharmacy University of Regensburg Universitätsstraße 31 93053 Regensburg Germany.
European J Org Chem. 2021 Mar 19;2021(11):1720-1725. doi: 10.1002/ejoc.202001673. Epub 2021 Mar 8.
The facile synthesis of aminoallenes, accomplished by a selenium-π-acid-catalyzed cross-coupling of an -fluorinated sulfonimide with simple, non-activated alkynes, is reported. Until now, aminoallenes were difficult to be accessed by customary means, inasmuch as pre-activated and, in part, intricate starting materials were necessary for their synthesis. In sharp contrast, the current study shows that ordinary internal alkynes can serve as simple and readily available precursors for the construction of the aminoallene motif. The operating reaction conditions tolerate numerous functional groups such as esters, nitriles, (silyl)ethers, acetals, and halogen substituents, furnishing the target compounds in up to 86 % yield.
报道了通过硒-π-酸催化的α-氟代磺酰亚胺与简单的非活化炔烃的交叉偶联实现氨基丙二烯的简便合成。到目前为止，通过常规方法很难获得氨基丙二烯，因为其合成需要预先活化且部分复杂的起始原料。与之形成鲜明对比的是，当前研究表明普通的内炔烃可作为构建氨基丙二烯结构单元的简单且易于获得的前体。该反应的操作条件能耐受多种官能团，如酯基、腈基、（硅烷基）醚、缩醛和卤素取代基，以高达86%的产率提供目标化合物。
