芳硒化铯与炔硒醚反应合成(Z)-1,2-二芳硒基烯

Synthesis of (Z)-1, 2-Bis(arylseleno)-1-alkene through the Reaction of Cesium Arylselenolate with Alkynyl Selenide

芳硒化钠与炔硒醚在室温不反应.但是,在室温、氮气保护下芳硒化铯与炔硒醚能有效的进行反应,立体选择生成(Z) 1,2 二芳硒基烯,产率在88%～95%.这表明ArSeCs中ArSe-具有较强的亲核性.本方法具有反应条件温和、产率高、不需无水条件、实验操作简单.这一方法为(Z) 1,2 二芳硒基烯的合成提供了一条新的有效的途径.

At room temperature, sodium arylselenolate does not react with alkynyl selenides. But cesium arylselenolate can react efficiently with alkynyl selenide in commercial tetrahydrofuran(THF) at room temperature under N2 to afford (Z)-1,2-Bis(arylseleno)-1-alkene with a yield of 88%～95%. This indicated that the ArSe^- in ArSeCs has a greater nucleophility than ArSe^- in ArSeNa. It may result from the less static electricity between ArSe^- and Cs+. The advantages of the present method include mild condition, high stereoselectivity and high yields. It provides an efficient and practical way for the synthesis of (Z)-1, 2-bis (arylseleno) -1-alkene.