We report a fluoride-initiated coupling reaction between trifluoromethylarenes and allylsilanes to access allylated alpha,alpha-difluorobenzylic compounds. This method's utility is demonstrated through a 30 mmol scale reaction, a sequential allylation/derivatization protocol and multiple examples of site-selective trifluoromethylarene allylation. Initial mechanistic studies suggest a base-induced single electron transfer pathway is responsible for the high efficiency and selectivity of this novel C-F substitution process.