The cobalt(III)-catalyzed chelation-assisted allylation of arene C–H bonds was accomplished by employing allyl carbonates. The important features of the present reaction include the use of directing groups such as pyrazoles and pyridines, wide functional-group tolerance, and the synthesis of various allylated (hetero)arenes in good to excellent yields. On the basis of the observations, a plausible mechanism is also proposed involving the formation of a π-allyl species. © 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim