The Ru-catalyzed meta-C-H benzylation of arenes bearing pyridyl, pyrimidyl, and pyrazolyl directing groups with toluene derivatives has been reported. Heptafluoroisopropyl iodide (iC3F7I) was employed as both a mild oxidant and radical initiator. This reaction showed excellent site-selectivity and tolerated a wide range of functional groups, providing a new strategy for the synthesis of various diarylmethane moieties.