Effect of fluorine substituents on catalytic functionalizations of alkyl halides with organostannanes

Introduction of fluorine atom(s) at the γ- and δ-positions of alkyl iodides increased the selectivities toward palladium-catalyzed cross-coupling reaction with organostannanes. A similar effect of fluorine substituents on the selectivities was also observed in the palladium-catalyzed carbonylative coupling reaction of alkyl iodides with phenyltributyltin under CO pressure.