Metallaphoto-catalysis has been established as a robust platform for efficient construction of a range of chemical bonds. Moreover, transformation of native functionalities such as C(sp3)-H bonds to produce functional molecules represents one of the most attractive strategies in organic synthesis. Merging two powerful methodologies, metallaphoto-catalyzed benzylic and allylic C(sp3)-H bond functionalizations provide a series of general and mild approaches for diversification of alkylbenzenes and alkenes.