作者:Shunsuke Fujie、Kouichi Matsumoto、Seiji Suga、Toshiki Nokami、Jun-ichi Yoshida
DOI:10.1016/j.tet.2010.02.049
日期:2010.4
ArS(ArSSAr)+ (arylbis(arylthio)sulfonium ions), which were generated and accumulated by the electrochemical oxidation of diaryl disulfides (ArSSAr) in CH2Cl2 at −78 °C, reacted with alkenes to give the corresponding diarylthio-substituted compounds in a stereospecific manner in good yields, when the reaction was quenched with a soft nucleophile, such as allylsilanes, ketene silyl acetals, and triethylamine
ArS(ArSSAr)+(芳基双(芳硫基)ulf离子)是通过在-78°C下于CH 2 Cl 2中对二芳基二硫化物(ArSSAr)进行电化学氧化而生成和积累的,与烯烃反应生成相应的二芳硫基取代当用柔软的亲核试剂(例如烯丙基硅烷,乙烯酮甲硅烷基乙缩醛和三乙胺)淬灭反应时,可以立体定向的方式以良好的收率得到化合物。已经提出了一种机制,该机制涉及初始形成epi离子,然后通过ArSSAr的攻击使环开环。还发生了ArS(ArSSAr)+与炔烃的反应,在相似条件下立体选择性地生成了1,2-二有机硫代取代的烯烃。