Synthesis of 3-Aryl Oxindoles having Trifluoromethylated Quaternary Stereocenters via Catalyst Free Arylation

被引：6
|
作者：
Nagababu, Chavakula [1 ,2 ]
Prudhviraj, Jaggaraju [1 ,2 ]
Punna, Nagender [1 ,2 ]
机构：
[1] Indian Inst Chem Technol CSIR IICT, Fluoro Agrochem Dept, CSIR, Hyderabad 500007, India
[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, India
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2023年 / 365卷 / 01期
关键词：
Oxindole; CF3-Substituted quaternary stereocenter; Anisoles; Arylation; 3-Trifluoromethyl indoline; ENANTIOSELECTIVE SYNTHESIS; DIASTEREOSELECTIVE SYNTHESIS; BMS-204352 MAXIPOST(TM); CONSTRUCTION; CYCLOADDITION; FLUORINE; DESIGN; ACCESS;
D O I：
10.1002/adsc.202200918
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
Herein we report the synthesis of 3-aryl oxindoles having trifluoromethylated quaternary stereocenters through the catalyst free arylation of 3-trifluoromethyl,3-tosyloxy oxindoles with anisoles. The transformation proceeds via electrophilic 3-(trifluoromethyl)-2H-indolium intermediate (Michael acceptor), which is generated by the heterolytic cleavage of C-OTs bond under metal-free conditions in PEG-400. The developed strategy offers broad substrate scope, extending to N,N-dimethyl-anilines, and thio-anisole to afford the range of 3-trifluoromethyl,3-aryl oxindoles in 62-91% yields.
引用
收藏
页码：8 / 12
页数：5
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