Premium
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.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom