A ruthenium-catalyzed alternative para- and meta-difluoroalkylation of anilines is herein reported. The reaction tolerates a broad range of aniline derivatives and provides a convenient approach for accessing the corresponding para/meta-selective difluoroalkylated products. Mechanism studies demonstrated that the initial CAr-H and N-H cycloruthenation is the pivotal step in achieving remote C-H difluoroacetylation.