The development of selective catalyst-controlled functionalization of alkyl halides and aliphatic C-H bonds (C(sp3)-X functionalization) is one of the grand challenges in organic synthesis. Realization of this goal will open the door to the development of new chiral centers and enable cost-effective methods to quickly increase molecular complexity en route to biologically active compounds, natural products, and pharmaceutical agents. In this talk, I will discuss recent progress in bridging computation and experiment to accelerate catalyst and reaction design for selective iron catalyzed C(sp3)-X functionalization reactions.