环苯基六炔烃的制备:脱Ph_2P(O)/分子内Eglington偶联环化反应  

Synthesis of Cyclic Phenyl Polyynes: Ph_2P(O)-Deprotection/Intramolecular Eglington Coupling Cyclization

作　　者：彭丽芬 张思维 王丙昊 寻梦硕 唐子龙 焦银春 许新华[2] 

机构地区：[1]湖南科技大学理论有机化学与功能分子教育部重点实验室精细聚合物可控制备及功能化应用湖南省重点实验室化学化工学院,湘潭411201 [2]湖南大学化学化工学院化学生物传感与计量学国家重点实验室,长沙410082

出　　处：《有机化学》2018年第2期519-525,共7页Chinese Journal of Organic Chemistry

基　　金：湖南省教育厅一般项目(No.17C0629);湖南科技大学博士启动基金(No.E51693);湖南科技大学理论有机化学与功能分子教育部重点实验室开放基金(No.E21630);国家自然科学基金(No.21402048)资助项目~~

摘　　要：脱二苯膦酰(Ph_2P(O))保护基/分子间炔烃偶联环化反应可一锅进行,高效形成环苯基六炔烃.与Haley等的脱硅基/Eglington偶联分步反应的制备方法相比,极性Ph_2P(O)保护基使产物与少量剩余原料具有不同极性而易分离,且本反应与产物Rf值相近的分子间偶联副产物量较少,使得产物易分离.且一锅反应可避免脱Ph_2P(O)的后处理,减少化合物损失,有效提高了环苯基六炔烃的产率.此外,本方法还具有中间体易制备、反应条件温和等优点.Ph_2 P（O）-deprotection/intramolecular Eglington coupling cyclization, proceeding in one-pot manner, can be applied to synthesize cyclic phenyl polyynes. Compared to Micheal M. Haley＇s stepwise desilylation/Eglington coupling reaction, the polar Ph_2 P（O） protecting group enabled facile seperation of product from remaining starting compound for their different polarity, and it also led to easy separation of target compound because the amont of by-products which showed similar Rf to target compound decreased. Furthermore, our one-pot reaction, avoiding the workup after Ph_2 P（O）-deprotection and reducing losses of materials, increased the yield of cyclic aromatic polyynes. This method showed some other outstanding features including easy synthesis of intermediates and mild reaction conditions.

关 键 词：一锅反应 二苯基膦酰基保护基 环苯基多炔烃 

分 类 号：O621.25[理学—有机化学]