无过渡金属催化的α-溴代茚酮自由基裂解反应合成(2-氰基苯基)乙酸-2,2,6,6-四甲基哌啶酯  

Synthesis of 2,2,6,6-Tetramethylpiperidin-1-yl-2-(2-cyanophenyl)-acetate by Transition Metal-Free Radical Cleavage Reaction from α-Bromoindanone

作　　者：秦娇 陈杰 苏艳[1] Qin Jiao;Chen Jie;Su Yan(State Key Laboratory of High-Efficiency Coal Utilization and Green Chemical Engineering,College of Chemistry and Chemical Engineering,Ningxia University,Yinchuan 750021)

机构地区：[1]宁夏大学化学化工学院,省部共建煤炭高效利用与绿色化工国家重点实验室,银川750021

出　　处：《有机化学》2023年第6期2171-2177,共7页Chinese Journal of Organic Chemistry

基　　金：宁夏自然科学基金(No.2021AAC03100)资助项目。

摘　　要：报道了溴代茚酮底物在叠氮化钠和2,2,6,6-四甲基哌啶氮氧化物共同作用下合成(2-氰基苯基)乙酸-2,2,6,6-四甲基哌啶酯的方法,实现了溴代茚酮结构在无过渡金属催化条件下的自由基裂解反应,合成了一系列芳基2-氰基-苯乙酸酯化合物,拓展了氰基苯乙酸酯的合成方法,并通过计算化学方法验证了这一反应的反应机理.该反应条件温和、无需过渡金属催化剂、操作简便以及具有一定的底物普适性.In this paper,the synthesis of 2,2,6,6-tetramethylpiperidin-1-yl-2-(2-cyanophenyl)acetate from bromoindanone with sodium azide and 2,2,6,6-tetramethylpiperidine nitrogen oxide was reported.The carbon-carbon bond cleavage of bromoindenone was realized with transition metal-free catalysis and a series of aryl 2-cyano-phenylacetate compounds were obtained.This method was an expansion of cyanophenylacetate' synthesis,and the reaction mechanism was verified by computational chemistry.The experiment was carried out under mild conditions with transition metal-free catalysis and with broad substrate scope.

关 键 词：茚酮 2-氰基苯乙酸酯 自由基裂解反应 无过渡金属 

分 类 号：O625.523[理学—有机化学]