We describe a direct, catalytic approach to the 1,2-difluorination of alkenes. The method utilizes a nucleophilic fluoride source and an oxidant in conjunction with an aryl iodide catalyst and is applicable to alkenes With all types of substitution patterns.. In general, the vicinal difluoride products are produced with high diastereoselectivities. The observed sense of stereo induction implicates anchimeric assistance pathways in reactions of alkenes bearing neighboring Lewis basic functionality.