可见光诱导下喹喔啉酮与吡咯衍生物的氧化偶联  

Visible-Light-Induced Regio-selective Oxidative Coupling of Quinoxalinones with Pyrrole Derivatives

作　　者：沈梦涵 李来强 周泉 王洁慧 王磊 Shen Menghan;Li Laiqiang;Zhou Quan;Wang Jiehui;Wang Lei(Advanced Research Institute and School of Pharmaceutical Sciences,Taizhou University,Taizhou,Zhejiang 318000;State Key Laboratory of Organometallic Chemistry,Shanghai Institute of Organic Chemistry,Chinese Academy of Sciences,Shanghai 200032)

机构地区：[1]台州学院高等研究院和药学院,浙江台州318000 [2]中国科学院上海有机化学研究所、金属有机化学国家重点实验室,上海200032

出　　处：《有机化学》2023年第2期697-704,共8页Chinese Journal of Organic Chemistry

基　　金：Project supported by the Natural Science Foundation of Zhejiang Province(No.LZ22B020003);the National Natural Science Foundation of China(No.22071171)。

摘　　要：发展了一种区域选择性的喹喔啉酮3-位氧化偶联富电子吡咯衍生物的方法.以Mes-Acr-Me^(+)ClO_(4)^(-)(3 mol%)为光敏剂,空气氧为氧化剂,高收率得到喹喔酮与吡咯衍生物的氧化偶联产物.该方法底物的官能团适用范围广,反应高效绿色,可快速构建基于喹喔啉酮-吡咯衍生物的药物分子库.相同测试条件下的Stern-Volmer荧光淬灭实验表明缺电子芳烃1-甲基喹喔啉酮对光敏剂的淬灭速率常数Kq=1.2×10^(9)L·mol^(-1)·s^(-1),而富电子芳烃1-甲基吡咯/1-甲基吲哚的淬灭常数约为1.06~1.07×10^(10)L·mol^(-1)·s^(-1),后者的荧光淬灭速率几乎是前者的10倍.Herein,one feasible methodology has been developed for oxidative cross-coupling between quinoxalinones and electron-rich aromatic rings(pyrroles or indoles).Utilizing the commerial available photocatalyst+Mes-Acr-Me^(+)ClO_(4)^(-)(3 mol%)as catalyst and air as external oxidant,the oxidative coupling products of quinolones and pyrrole derivatives were obtained in high yields.The protocol provides effective acceess to such quinoxalinones-pyrrole derivatives with profiles of broad functional group,efficient conversion and easy-handling.Furthermore,Stern-Volmer fluorescent quenching experiments under the same condition disclosed that quenching rate constant of electron-rich aromatic ring(pyrrole or indole,kq 1.06×10^(10)~1.07×10^(10)L•mol^(-1)•s^(-1))was nearly one order of magnitude larger than that of electro-deficient quinoxalinones(kq=1.2×10^(9)L•mol^(-1)•s^(-1)).

关 键 词：氧化偶联 喹喔啉酮 光催化 区域选择性 

分 类 号：O626[理学—有机化学]