Na2S2O4-promoted radical addition reaction of perfluoroalkyl iodides with allenes and the Pd(0)-catalyzed stereoselective Sonogashira coupling reaction of addition products with propargyl alcohol

摘要

A Na2S2O4-promoted radical addition reaction of perfluoroalkyl iodides with allenes affording 1-perfluoroalkyl-2-alken-2-yl iodides 3 in 52-69% yields has been developed. Kinetic resolution of the Z/E mixture via the Pd(0)-catalyzed Sonogashira coupling reaction was applied to prepare pure vinylic iodides (Z)-3 and the related coupling products (E)-4 up to 98:2 E/Z ratio.