Synthesis of 5-substituted pyrimidine nucleosides through a palladium-catalyzed cross-coupling of alkenylhalosilanes

Palladium-catalyzed cross-coupling of alkenylhalosilanes with 5-iodouracil and 5-iodouridine derivatives was described. 5-Iodo-1,3-dimethyluracil coupled with alkenylfluorodimethylsilanes to give the corresponding cross-coupled products in good yield. Fully protected 5-iodo-2′-deoxyuridine derivative also underwent the cross-coupling reaction. Noteworthy is that unprotected 5-iodo-2′-deoxyuridine could be converted into the corresponding cross-coupled products in good yields using alkenyl(difluoro)methylsilanes.