Transition metal-catalyzed directed C-H functionalization has recently emerged as a promising step-economic strategy for the synthesis of diverse range of structures. Heterocycles have been the center of focus in this nascent field for their role as privileged pharmaceutical scaffolds. Forward reactivity analysis, a process of streamlining multi-step reaction steps/pathways in silico based on projected matching of reactivity between directing groups and coupling partners, can instill an element of rationality into reaction design. However, this level of reasoning has not been routinely practiced in the context of appendage planning.