Faculty of Chemistry, Kharazmi University, P. O. Box 15719-14911, 49 Mofateh Street, Tehran, Iran.
Chem Commun (Camb). 2019 Jan 24;55(9):1253-1255. doi: 10.1039/c8cc09726g.
A highly regio- and stereocontrolled procedure for the synthesis of vinyl dithiocarbamates via catalyst-free hydrothiolation of unactivated alkynes with in situ prepared dithiocarbamic acids with total atom economy is reported. While unactivated terminal alkynes afforded the Markovnikov adducts with excellent regioselectivity, ethynyltrimethylsilane furnished the E-selective anti-Markovnikov adducts with excellent regio- and stereoselectivity. In addition, the obtained vinyl dithiocarbamates were applied as efficient precursors for the synthesis of secondary thiols and α-hydroxythioamides.
本文报道了一种通过未活化炔烃与原位制备的二硫代氨基甲酸盐的无催化剂氢硫加成反应，以总原子经济性高区域和立体选择性合成乙烯基二硫代氨基甲酸盐的方法。非活化末端炔烃以优异的区域选择性提供 Markovnikov 加成产物，而乙炔基三甲基硅烷则以优异的区域和立体选择性提供 E-选择性反 Markovnikov 加成产物。此外，得到的乙烯基二硫代氨基甲酸盐可用作合成仲硫醇和α-羟硫酰胺的有效前体。
