Palladium-Catalyzed Deaminative Phenanthridinone Synthesis from Aniline via C-H Bond Activation

被引:44
|
作者
Yedage, Subhash L. [1 ]
Bhanage, Bhalchandra M. [1 ]
机构
[1] Inst Chem Technol, Dept Chem, Bombay 400019, Maharashtra, India
来源
JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 10期
关键词
ORTHO-ARYLATION; N-METHOXYBENZAMIDES; AMINATION REACTION; ARYL; HECK; AMIDES; PROTOBERBERINE; OLEFINS; SILICA; AMINES;
D O I
10.1021/acs.joc.6b00378
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This work reports palladium-catalyzed phenanthridinone synthesis using the coupling of aniline and amide by formation of C-C and C-N bonds in a one-pot fashion via dual C-H bond activation. It involves simultaneous cleavage of four bonds and the formation of two new bonds. The present protocol is ligand-free, takes place under mild reaction conditions, and is environmentally benign as nitrogen gas and water are the only side products. This transformation demonstrates a broad range of aniline and amide substrates with different functional groups and has been scaled up to gram level.
引用
收藏
页码:4103 / 4111
页数:9
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