Synthesis of Phenanthridines through Palladium‐Catalyzed Cascade Reaction of 2‐Halo‐N‐Ms‐arylamines with Benzyl Halides/Sulfonates

• Published in: European journal of organic chemistry Vol. 2017; no. 5; pp. 996 - 1003
• Main Authors: Yang, Si‐Yi, Han, Wen‐Yong, Zhang, Ding‐Lei, Zhou, Xiao‐Jian, Bai, Mei, Cui, Bao‐Dong, Wan, Nan‐Wei, Yuan, Wei‐Cheng, Chen, Yong‐Zheng
• Format: Journal Article
• Language: English
• Published: Weinheim Wiley Subscription Services, Inc 03-02-2017
• Subjects: Cascade reactions; C–H activation; Nitrogen heterocycles; Nucleophilic substitution; Palladium
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201601608

An efficient palladium‐catalyzed nucleophilic substitution/C–H activation/aromatization cascade reaction between readily available 2‐halo‐N‐Ms‐arylamines (Ms = methanesulfonyl) and benzyl halides/sulfonates has been described. A wide variety of phenanthridines were synthesized in a one‐pot fashion in moderate to high yields (37–86 %). Notably, this method provides a straightforward, facile approach for the synthesis of phenanthridines. The practicality was further substantiated by successfully carrying out a gram‐scale preparation.
A facile and efficient palladium‐catalyzed nucleophilic substitution/C–H activation/aromatization cascade reaction for the construction of phenanthridines has been explored. This work provides a practical protocol to obtain phenanthridines in moderate to high yields (37–86 %) from readily available 2‐halo‐N‐Ms‐arylamines (Ms = methanesulfonyl) and benzyl halide/sulfonate substrates.