Li Lun, Wasik Kimberly A, Frost Brian J, Geary Laina M
University of Nevada, Reno, Department of Chemistry, Reno, Nevada, 89557, USA.
Tetrahedron Lett. 2020 Jan 9;61(2). doi: 10.1016/j.tetlet.2019.151370. Epub 2019 Nov 6.
The silver-catalyzed reaction of silyl enol ethers with dichloroacetylene (DCA) is described. When DCA was used as a solution in diethyl ether, we found that the silyl group was transferred to the vinyl group, resulting in stereochemically pure tetrasubstituted olefins. However, when DCA was used as a solution in the more polar acetonitrile, protonation was the major pathway, and trisubstituted olefins were the dominant products.
描述了硅基烯醇醚与二氯乙炔（DCA）的银催化反应。当DCA以在乙醚中的溶液形式使用时，我们发现硅基转移到了乙烯基上，生成了立体化学纯的四取代烯烃。然而，当DCA以在极性更强的乙腈中的溶液形式使用时，质子化是主要途径，三取代烯烃是主要产物。
