Ruthenium(II)carboxylate complexes enabled the unprecedented direct C鈥揌 arylation of azoarenes with aryl halides through chelation assistance. The mild reaction conditions of the optimized C鈥揌 functionalization process resulted in a remarkable functional group tolerance. The proximity-induced C鈥揌 arylation proceeded with high positional selectivity and could be performed in a one-pot protocol along with a azoarene reduction, providing expedient access to ortho-arylated anilines.