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A simple, straightforward strategy for the synthesis of polyheterocyclic compounds (PHCs) is reported, which involves iterative cycles of palladium-catalyzed Sonogashira coupling, followed by iodocyclization using I2 or ICl. A variety of heterocyclic units, including benzofurans, benzothiophenes, indoles and isocoumarins, can be efficiently incorporated under mild reaction conditions. In addition, variations of this strategy afford a variety of linked and fused PHCs.

Palladium-catalyzed and electrophilic cyclization approaches to important heterocycles and carbocycles