Wu Jin-Ji, Xu Jia, Zhao Xiaodan
Institute of Organic Chemistry & MOE Key Laboratory of Bioinorganic and Synthetic Chemistry, School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou, 510275, P.R. China.
Chemistry. 2016 Oct 17;22(43):15265-15269. doi: 10.1002/chem.201603975. Epub 2016 Sep 15.
The efficient regio- and stereoselective construction of tetrasubstituted alkenes is challenging and very important. For this purpose, we have developed an efficient approach to synthesize tetrasubstituted trifluoromethylthiolated alkenes from simple alkynes in excellent regio- and stereoselectivities by selenide-catalyzed multicomponent coupling. Using this method, trifluoromethylthiolated alkenyl triflates and arenes were achieved. In particular, the triflates could be further converted into carbofunctionalized alkenes by palladium-catalyzed cross-coupling reactions. Our method provides a new pathway for the construction of trifluoromethylthiolated tricarboalkenes. This work presents the first example of selenide-catalyzed trifluoromethylthiolation of alkynes and enables the challenging functionalizations of alkynes.
四取代烯烃的高效区域和立体选择性构建具有挑战性且非常重要。为此，我们开发了一种有效的方法，通过硒化物催化的多组分偶联，从简单炔烃中以优异的区域和立体选择性合成四取代三氟甲硫基化烯烃。利用该方法，实现了三氟甲硫基化烯基三氟甲磺酸酯和芳烃。特别地，三氟甲磺酸酯可通过钯催化的交叉偶联反应进一步转化为碳官能化烯烃。我们的方法为构建三氟甲硫基化三碳烯烃提供了一条新途径。这项工作展示了硒化物催化炔烃三氟甲硫基化的首个实例，并实现了具有挑战性的炔烃官能化。
