芳基碘介导的缺电子烯烃电化学氮杂环丙烷化反应  

Aryl-Iodide-Mediated Electrochemical Aziridination of Electron-Deficient Alkenes

作　　者：刘峰 戴洁 程旭 Liu Feng;Dai Jie;Cheng Xu(National Demonstration Center for Experimental Chemistry Education,Jiangsu Key Laboratory of Advanced Organic Materials,Institute of Chemistry and Biomedical Sciences,School of Chemistry and Chemical Engineering,Nanjing University,Nanjing 210023)

机构地区：[1]南京大学化学化工学院化学与生物医学科学研究所江苏省先进有机材料重点实验室国家级化学实验教学示范中心,南京210023

出　　处：《有机化学》2021年第10期4014-4020,共7页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(Nos.22071105,22031008)资助项目.

摘　　要：氮杂环丙烷在药物分子的设计合成中有广泛应用.利用电化学方法合成氮杂环丙烷的研究主要集中于富电子烯烃的底物.利用芳基碘化物介导,以邻苯二甲酰肼为氮源,在连通池中实现了缺电子烯烃的氮杂环丙烷化.高价碘稳定的氮宾及酰化羟肼可能是原位产生的活性氮源试剂,它们通过分步的过程实现三元环的构建.一系列α,β-不饱和酯、酰胺、腈和酮都可以通过这个电化学方法转化为对应的氮杂环丙烷.A protocol of electrochemical aziridination of electron-deficient alkenes was reported using phthalhydrazide as nitrogen source.The reaction could be conducted in undivided cell,and the ArI is essential to achieve the transformation.Hypervalent-iodine-stablized nitrene and acetyl hydroxyhydrazine were suggested as the in-situ generated nitrogen source for the stepwise aziridination.This protocol can be applied to the azirdination ofα,β-unsaturated esters,amides,nitrile and ketones to give a series N-containing molecules.

关 键 词：电化学 氮杂环丙烷 高价碘 缺电子烯烃 

分 类 号：TQ460.1[化学工程—制药化工]