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Paper | Regular issue | Vol 94, No. 9, 2017, pp.1693-1706
Published online, 12th July, 2017
DOI: 10.3987/COM-17-13754
Synthesis of Highly Substituted 5,6-Dihydrobenzo[j]phenanthridine Derivatives via Domino Reaction

Yuqin Wu, Lidong Li, Liangyun Yu, Zhang Qi, Feng Xue, and Xu Qi*

*School of Chemistry and Chemical Engineering, Yancheng Institute of Technology, Jianjun East Road No. 211, Yancheng 224051, China

Abstract

An atom-economical method for diynes with aryl halides under palladium-catalyzed conditions has been developed. Using unactivated simple diynes with aryl halides in the presence of palladium catalytic system afforded various 7,12-diphenyl-5-tosyl-5,6-dihydrobenzo[j]phenanthridine derivatives through C–C coupling and C–H bond activation in one step. This cascade reaction was initiated by an intermolecular [2 + 2 + 2] cycloaddition.