可见光诱导α-重氮酯的脱氮氧合反应构建α-氧代酰亚胺酯  

Visible-Light-Induced Denitrification Oxygenation Reaction ofα-Diazoesters to Constructα-Oxyimido Esters

作　　者：刘瑞生 付双敏 楚秀民 张灵莉 丁柔 赵先恩[1] 岳会兰[2] 魏伟[1,2] Liu Ruisheng;Fu Shuangmin;Chu Xiumin;Zhang Lingli;Ding Rou;Zhao Xian'en;Yue Huilan;Wei Wei(School of Chemistry and Chemical Engineering,Qufu Normal University,Qufu,Shandong 273165;CAS Key Laboratory of Tibetan Medicine Research,Northwest Institute of Plateau Biology,Chinese Academy of Sciences,Xining,Qinghai 810008)

机构地区：[1]曲阜师范大学化学与化工学院,山东曲阜273165 [2]中国科学院藏药研究重点实验室,中国科学院西北高原生物研究所,青海西宁810008

出　　处：《有机化学》2022年第8期2462-2470,共9页Chinese Journal of Organic Chemistry

基　　金：国家级大学生创新创业训练项目(No.S202110446110);山东省高校青创科技计划(No.2019KJC021);山东省自然科学基金(No.ZR2021MB065);国家自然科学基金(Nos.22176109,31900298);青海省创新平台建设专项(No.2022-ZJ-Y03)资助项目。

摘　　要：报道了一种可见光诱导下α-重氮酯与N-羟基邻苯二甲酰亚胺(NHI)的脱氮氧合反应构建α-氧代酰亚胺酯化合物的方法.该反应采用3W蓝色LEDs灯为可见光源,无需任何光催化剂,室温下在1,4-二氧六环溶剂中可以有效合成一系列α-氧代酰亚胺酯化合物.有趣的是,当四氢呋喃作为溶剂时,四氢呋喃参与的三组分开环产物可以获得中等至良好的收率.该反应放大到克级规模仍保持良好的反应效率,表明该方法具有合成α-氧代酰亚胺酯的实际应用潜力.Visible-light-induced denitrification oxygenation reaction ofα-diazoesters with N-hydroxyimides to accessα-oxyimido esters has been developed.This reaction provides an efficient approach to synthesize a series of N-hydroxyimides at room temperature in 1,4-dioxane under irradiation of 3 W blue LED lamps without any photocatalyst.Interestingly,when tetrahydrofuran(THF)was used as the solvent,structurally diverseα-oxyimido esters could be rapidly and efficiently obtained through a three-component coupling reaction ofα-diazoesters,THF,and N-hydroxyimides.The reaction could conduct on a gram scale without a significant loss of reaction efficiency,indicating that this method could serve as a practical protocol to synthesizeα-oxyimido esters.

关 键 词：可见光 α-重氮酯 N-羟基邻苯二甲酰亚胺 α-氧代酰亚胺酯 

分 类 号：O623.626[理学—有机化学]