Palladium-Catalyzed Synthesis of Benzophenanthrosilines by C-H/C-H Coupling through 1,4-Palladium Migration/Alkene Stereoisomerization.

A new and efficient synthesis of 8H-benzo[e]phenanthro[1,10-bc]silines from 2-((2-(arylethynyl)aryl)silyl)aryl triflates under palladium catalysis has been developed. The reaction mechanism was experimentally investigated and a catalytic cycle involving C-H/C-H coupling through a new mode of 1,4-palladium migration with concomitant alkene stereoisomerization is proposed.