Trifunctionalization of CC bonds in vinyl azides to access densely functionalized phenanthridines enabled by the NCS/AgNO 2 system.

An unprecedented trifunctionalization of CC bonds in 2-(1-azidovinyl)-1,1'-biphenyls has been successfully achieved using the NCS/AgNO 2 system, leading to the preparation of 6-(dichloro(nitro)methyl)phenanthridines in moderate to good yields. In this process, the NCS/AgNO 2 system serves as a NO 2 radical initiator as well as a chloro group source. The present protocol is a rare example of the selective construction of densely functionalized phenanthridine derivatives in a one-pot manner.