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Practical Synthesis of Phenanthridinones by Palladium‐Catalyzed One‐Pot C–C and C–N Coupling Reaction: Extending the Substrate Scope to o ‐Chlorobenzamides
Author(s) -
Liu Hailong,
Han Weibiao,
Li Chun,
Ma Zhiyong,
Li Ruixiang,
Zheng Xueli,
Fu Haiyan,
Chen Hua
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501170
Subject(s) - chemistry , palladium , catalysis , substrate (aquarium) , combinatorial chemistry , yield (engineering) , cascade reaction , phosphine , coupling reaction , domino , scope (computer science) , dimethylacetamide , organic chemistry , solvent , computer science , oceanography , materials science , metallurgy , geology , programming language
A highly efficient construction of phenanthridinone derivatives from o ‐halobenzamides was developed by using a phosphine‐free palladium catalyst in N , N ‐dimethylacetamide. The domino reaction proceeds through a sequential C–C and C–N bond‐formation process in one pot. This protocol exhibits broad substrate scope and affords a series of phenanthridinones in up to 93 % yield. Importantly, the protocol could also be applied for the less reactive o ‐chlorobenzamides. The approach constitutes the first example of the synthesis of phenanthridinones from this kind of substrate. Moreover, the success of a gram‐scale reaction demonstrated that this operationally simple process is scalable.