An atom transfer radical addition elimination (ATRE) reaction of terminal alkenes with perfluoroalkyl halides under visible light is described. The photoredox catalysis with Eosin Y provides perfluoroalkenes in good yields. The reaction has been utilized for the late stage perfluoroalkenylation of an estrone-derived alkene.
The reduction of alkenyl halides with tributyltinhydride in the presence of a catalytic amount of tetrakis(triphenylphosphine)palladium has been studied. Alkenyl iodides reacted easily with tributyltinhydride at 25°C to give the corresponding hydrocarbons stereoselectively. However, the reaction of alkenyl bromides were sluggish at 25°C and needed heating at 75°C to complete.