Organic letters

Arylative Cyclization of 2-Isocyanobiphenyls with Anilines: One-Pot Synthesis of 6-Arylphenanthridines via Competitive Reaction Pathways

Z Xia, J Huang, Y He, J Zhao, J Lei, Q Zhu

Index: Xia, Zhonghua; Huang, Jinbo; He, Yimiao; Zhao, Jiaji; Lei, Jian; Zhu, Qiang Organic Letters, 2014 , vol. 16, # 9 p. 2546 - 2549

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Citation Number: 56

Abstract

A transition-metal-free method for the synthesis of C6 phenanthridine derivatives by arylative cyclization of 2-isocyanobiphenyls with arylamines in one pot was developed. Mechanistic studies suggest that electrophilic aromatic substitution (SEAr) of a nitrilium intermediate and homolytic aromatic substitution (HAS) of an imidoyl radical intermediate are two competitive reaction pathways involved in the annulation step.