Stereospecific Synthesis of （Z）-α-Fluoro-β-trifluoromethyl Vinyl Iodides and Their Application to the Synthesis of Polyfluorinated Thienyl Alkadienes  

作　　者：沈延昌 王国平 

机构地区：[1]State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry Chinese Academy of Sciences, Shanghai 200032, China

出　　处：《Chinese Journal of Chemistry》2006年第9期1242-1246,共5页中国化学（英文版）

摘　　要：The direct iodination of polyfluorinated vinyl stannanes by tin-iodine exchange methodology was achieved giving （Z）-α-fluoro-β-trifluoromethyl vinyl iodides stereospecifically. Changing the substituent in R group from the electron-withdrawing group to electron-donating group led to an increase in the yield from 78% to 90%, while it was moved from para to meta position the reaction did not afford a dramatic change in the yield （90% to 95%）. In addition, this reaction also can be applied to the vinyl stannane with heterocyclic group. The further coupling reaction of prepared vinyl iodide containing heterocyclic moiety with （Z）-α-fluoro-β-trifluoromethylstannanes gave polyfluorinated heterocyclic alkadienes with 2E,4E-selectivity.The direct iodination of polyfluorinated vinyl stannanes by tin-iodine exchange methodology was achieved giving （Z）-α-fluoro-β-trifluoromethyl vinyl iodides stereospecifically. Changing the substituent in R group from the electron-withdrawing group to electron-donating group led to an increase in the yield from 78% to 90%, while it was moved from para to meta position the reaction did not afford a dramatic change in the yield （90% to 95%）. In addition, this reaction also can be applied to the vinyl stannane with heterocyclic group. The further coupling reaction of prepared vinyl iodide containing heterocyclic moiety with （Z）-α-fluoro-β-trifluoromethylstannanes gave polyfluorinated heterocyclic alkadienes with 2E,4E-selectivity.

关 键 词：tin-iodine exchange reaction （Z）-α-fluoro-β-trifluoromethylstannane （Z）-α-fluoro-β-trifluoromethylvinyl iodide polyfluorinated heterocyclic alkadiene 

分 类 号：O627.7[理学—有机化学]