Magnesium Selenolate Reaction Research

Organoselenium compounds show good biological activity, and selenides are important compounds of them. There are many disadvantages for methods of selenides synthesis so far. Based on the former research works, we used magnesium selenolate as reactant to react with RX or styrene to synthesize a series of selenide. Followings are the main research results:1. Some symmetrical selenides, such as di-4-methoxyphenyl selenide, di-2-methoxyphenyl selenide,2-(2-thienylseleno)thiophene, di-1-naphthyl selenide and di-cyclohexyl selenide were successfully synthesized by this method in yields of 94%,51%,13%,19%and 20%, respectively.2. Some unsymmetrical selenides were successfully synthesized by this method, but complex products were given. The effects of different conditions on the reaction were investigated. We also discuss the reaction mechanism. After R1SeMgBr was prepared from R1Br, then the added R2Br reacted with excess Mg to afford R2MgBr. Se of R1SeMgBr could exchange to R2MgBr to form R2SeMgBr. Finally, the magnesium selenolates could react with Grignard reagents to generate complex selenides.3. (1-Phenyl)ethyl phenyl selenide was successfully synthesized from PhSeMgBr and styrene. It was found that magnesium selenolates reacting with styrene via the catalysis of CuI in the THF-H2O mixed solvent leaded to 40%yield of target product.