"Developing synthetic strategies and protocols that will enable direct functionalization of C-H bonds is of great interest to the organic chemist. The high stability (CSp2-H =110kcal/mol) and inert nature of these bonds makes them challenging. Currently, the major approaches used in catalytic C-H activation involves 1). The use of special ligands on the metal catalyst and 2). the use of directing groups (DGs) on the substrate. Notable strategies and transformations have been developed using the former which generally requires pre-activated substrates, high catalyst loading, harsh reaction conditions among other unfriendly environmental issues which is of great concern to the green chemist and the world at large. Despite the progress made in this area, achieving regioselectivity is still a major challenge. Improving the synthetic toolbox enabling activation of less functionalized substrates in a greener manner will minimize both waste production and energy consumption. Two similar tridentate directing groups derived from glycine and 8-aminoquinoline were shown to enable the palladium-catalyzed anti-Markovnikov hydrofunctionalization of 4-pentenylamine with drastically different efficiencies. A computational investigation into the origin of the reactivity difference between these isomeric, carbonyl-transposed auxiliaries suggests that protonation state, thus charge of the substrate-metal complex prior to nucleopalladation is key. These investigations have culminated in a directing group design that can undergo Pd-catalyzed hydrofunctionalization under relatively mild conditions, as low as room temperature."