Skhiri Aymen, Salem Ridha Ben, Soulé Jean-François, Doucet Henri
Institut des Sciences Chimiques de Rennes, UMR 6226 CNRS-, Université de Rennes 1, "Organométalliques: Matériaux et Catalyse", Campus de Beaulieu, 35042, Rennes, France.
Laboratoire de Chimie Organique Physique (UR 11ES74), Université de Sfax, Faculté des Sciences de Sfax, Route de la Soukra km 4, 3038, SFax, Tunisia.
Chemistry. 2017 Feb 24;23(12):2788-2791. doi: 10.1002/chem.201700202. Epub 2017 Feb 6.
Several reported methods allow access to α-arylated selenophenes, whereas the synthesis of β-arylated selenophenes remains very challenging. Here, the Pd-catalysed coupling of benzenesulfonyl chlorides with selenophenes affording regiospecific β-arylated selenophenes is reported. The reaction proceeds with easily accessible catalyst, base and substrates, and tolerates a variety of substituents both on the benzene and selenophene moieties. This transformation allows the programmed synthesis of polyarylated selenophenes with potential applications in pharmaceutical and materials chemistry, as the installation of aryl groups at the desired positions can be achieved.
已有几种报道的方法可用于合成α-芳基化硒吩,而β-芳基化硒吩的合成仍然极具挑战性。本文报道了钯催化苯磺酰氯与硒吩的偶联反应,可区域选择性地生成β-芳基化硒吩。该反应使用易于获得的催化剂、碱和底物,并且对苯环和硒吩部分上的各种取代基均具有耐受性。这种转化使得多芳基化硒吩的程序化合成成为可能,在药物化学和材料化学中具有潜在应用,因为可以在所需位置实现芳基的引入。