邻位酰胺基导向的共轭烯炔烃的二碘化-水化反应  

Ortho-amide-directed diiodohydration of conjugated enynes

作　　者：林川凯 张彩霞[1] 黄棵棵 王玉超 刘晋彪[1] LIN Chuankai;ZHANG Caixia;HUANG Keke;WANG Yuchao;LIU Jinbiao(Faculty of Materials Metallurgy and Chemistry,Jiangxi University of Science and Technology,Ganzhou 341000,Jiangxi,China)

机构地区：[1]江西理工大学材料冶金化学学部,江西赣州341000

出　　处：《江西理工大学学报》2020年第5期1-5,共5页Journal of Jiangxi University of Science and Technology

基　　金：国家自然科学基金资助项目(21502075);国家级大学生创新创业训练计划项目(201910407015)。

摘　　要：文章旨在开发一种邻位酰胺基导向的共轭烯炔烃的二碘化-水化反应,实现共轭烯炔烃的选择性官能团化。该反应只需N-碘代丁二酰亚胺作为碘代试剂,无须外加催化剂,常温下即可发生,产率较高。反应机理为:碘正离子与共轭烯炔烃发生亲电加成,形成炔丙基正离子中间体;随后,中间体发生分子内的酰胺羰基氧亲核环化;最终水解-碘代实现了共轭烯炔烃的选择性多官能团化。文章创新之处在于利用邻位酰胺基导向,实现共轭烯炔烃的选择性二碘化-水化反应。An ortho-amide-directed diiodohydration of conjugated enynes has been developed to achieve a series of regioselective functionalization of conjugated enyne.This protocol only needs N-iodosuccinimide(NIS)as an iodine reagent,without any other catalysts,providing high yield in mild conditions.The mechanism is proposed for this reaction.First,the propargyl cation is generated from the regioselectively electrophilic addition of I+with conjugated enynes.Subsequently,the intermediate undergoes an intramolecular nucleophilic cyclization.Finally,the desired product can be formed through the diiodohydration of the intermediate.The innovation of this paper is to realize the selective diiodohydration of conjugated enynes with the guidance of the ortho-amide group.

关 键 词：邻位酰胺基 N-碘代丁二酰亚胺 共轭烯炔烃 二碘化-水化反应 

分 类 号：O62[理学—有机化学]