苯乙烯的同步硒化和烯基化反应  

Simultaneous selenenylation and alkenylation of styrenes

作　　者：王利敏 胡博[1] 张万轩[1] WANG Limin;HU Bo;ZHANG Wanxuan(College of Chemistry and Chemical Engineering,Hubei University, Wuhan 430062, China)

机构地区：[1]湖北大学化学化工学院,湖北武汉430062

出　　处：《湖北大学学报（自然科学版）》2022年第2期214-219,共6页Journal of Hubei University：Natural Science

基　　金：有机功能分子合成与应用教育部重点实验室项目(KLSAOFM1912)资助。

摘　　要：有机硒化合物在有机合成中应用广泛,研究向分子中引入硒的方法具有重要意义.在含氟氧化剂(Selectfluor)存在下,二苯基二硒醚与苯乙烯类物质发生加成反应,实现苯硒化.苯乙烯的碳碳双键与亲电性有机硒化物发生加成反应的同时,另一苯乙烯分子参与加成反应,生成β-碳连有苯硒基,α-碳连有烯基的产物,使苯乙烯类物质同时实现苯硒化和烯基化.在反应中加入三甲基氰基硅烷,反应产率明显提高.研究表明,以乙腈作为溶剂,加入三甲基氰基硅烷作为添加剂,在80℃进行反应时,苯乙烯类物质的反应产率为37%~58%.烷基烯如3-溴丙烯,1-己烯不能发生此反应.Organoselenium compounds are widely used in organic synthesis,and it is important to develop the method for introducing selenium into molecules.In the presence of a fluoro-oxidant(Selectfluor),Phenylselenenylation was realized by the addition reaction of diphenyl diselenides with styrene.Diphenyl diselenide reacted with styrenes to form products containingβ-phenylselenyl andα-phenylethenyl,while a carbon-carbon double bond of styrene was added by a electrophilic phenylselenide and another molecule of styrene.Thus the selenenylation and alkenylation could be realized simultaneously for the styrenes.The yields could be improved obviously by adding trimethylcyanosilane into the reaction mixture.It was showed that when acetonitrile was used as a solvent and trimethylcyanosilane was added as an additive,the yields for the reactions of styrenes were 37%-58%at 80℃.Alkylenes such as 3-bromopropene and 1-hexene can't undergo this reaction.

关 键 词：含氟氧化剂(Selectfluor) 三甲基氰基硅烷 苯乙烯 硒化 

分 类 号：O627.6[理学—有机化学]