Synthesis of Bicyclic p-Diiodobenzenes via Silver-Catalyzed Csp-H Iodination and Ruthenium-Catalyzed Cycloaddition

Highly substituted iodobenzenes were efficiently and regioselectively synthesized from readily available 1,6-diynes via two-step process consisting of silver-catalyzed Csp-H iodination and subsequent ruthenium-catalyzed [2 + 2 + 2] cycloaddition of resultant iododiynes. Some of the obtained iodobenzenes were subjected to palladium-catalyzed C−C bond-forming reactions such as Mizoroki−Heck reaction, Sonogashira reaction, and Suzuki−Miyaura coupling, giving highly conjugated molecules.