Tandem Radical Cyclization for the Construction of Difluoro-Containing Oxindoles and Quinoline-2,4-diones

被引:27
作者
Ding, Fangwei [1 ,2 ]
Fang, Yuanding [2 ]
Jiang, Yanqiu [1 ]
Lin, Kaifeng [1 ]
Shi, Lei [1 ,2 ]
机构
[1] Harbin Inst Technol, MIIT Key Lab Crit Mat Technol New Energy Convers, Sch Chem & Chem Engn, Harbin 150001, Heilongjiang, Peoples R China
[2] Harbin Inst Technol, Shenzhen Grad Sch, Shenzhen 518055, Peoples R China
关键词
cyclization; difluoromethylation; oxindoles; quinolines; radical reactions; LIGHT PHOTOREDOX CATALYSIS; COPPER-MEDIATED DIFLUOROMETHYLATION; C-H DIFLUOROACETYLATION; ACTIVATED ALKENES; ADDITION/CYCLIZATION CASCADE; N-ARYLACRYLAMIDES; CARBOXYLIC-ACIDS; ACCESS; ARYL; QUINOLINE-2,4(1H,3H)-DIONES;
D O I
10.1002/asia.201701780
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Cu-catalyzed direct difluoromethylation of activated alkenes through a difluoromethyl radical addition/cyclization to afford difluorinated oxindoles and quinoline-2,4-diones has been developed. This method provides convenient access to a variety of oxindoles and quinoline-2,4-diones under mild conditions via a proposed tandem radical cyclization process, while tolerating various functional groups well. Moreover, a facile method to construct diverse difluorinated quinoline-2,4-diones by visible-light photoredox catalysis under mild conditions was presented.
引用
收藏
页码:636 / 640
页数:5
相关论文
共 60 条
[1]   Recent Advances of the Access to Indolinones via C-H Bond Functionalization/Cyclization Cascade Strategy [J].
Abdukader, Ablimit ;
Zhang, Yonghong ;
Zhang, Zengpeng ;
Liu, Chenjiang .
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2016, 36 (05) :875-888
[2]  
[Anonymous], 2014, ANGEW CHE
[3]  
[Anonymous], 2007, ANGEW CHEM, DOI DOI 10.1103/PHYSREVLETT.112.077206
[4]   Recent Progress toward the Introduction of Functionalized Difluoromethylated Building Blocks onto C(sp2) and C(sp) Centers [J].
Belhomme, Marie-Charlotte ;
Besset, Tatiana ;
Poisson, Thomas ;
Pannecoucke, Xavier .
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (37) :12836-12865
[5]   Copper Catalyzed β-Difluoroacetylation of Dihydropyrans and Glycals by Means of Direct C-H Functionalization [J].
Belhomme, Marie-Charlotte ;
Poisson, Thomas ;
Pannecoucke, Xavier .
ORGANIC LETTERS, 2013, 15 (13) :3428-3431
[6]   Copper-catalyzed olefinic C-H difluoroacetylation of enamides [J].
Caillot, Gilles ;
Dufour, Jeremy ;
Belhomme, Marie-Charlotte ;
Poisson, Thomas ;
Grimaud, Laurence ;
Pannecoucke, Xavier ;
Gillaizeau, Isabelle .
CHEMICAL COMMUNICATIONS, 2014, 50 (44) :5887-5890
[7]   Controlled Fluoroalkylation Reactions by Visible-Light Photoredox Catalysis [J].
Chatterjee, Tanmay ;
Iqbal, Naeem ;
You, Youngmin ;
Cho, Eun Jin .
ACCOUNTS OF CHEMICAL RESEARCH, 2016, 49 (10) :2284-2294
[8]   Tandem Radical Cyclization of N-Arylacrylamides: An Emerging Platform for the Construction of 3,3-Disubstituted Oxindoles [J].
Chen, Jia-Rong ;
Yu, Xiao-Ye ;
Xiao, Wen-Jing .
SYNTHESIS-STUTTGART, 2015, 47 (05) :604-629
[9]  
Fan J.-H., 2013, ANGEW CHEM, V125, P3726
[10]  
Feng Z., 2015, ANGEW CHEM, V127, P1286