The development of new reactions and catalysts for the oxidative cross-coupling of C-H bonds with C-H, N-H and O-H bonds will be discussed. Strategically, these reactions allow for the synthesis of complex molecules from their constituent components, minimizing the need for functional group activation and manipulation. Specifically, rhodium and iridium catalysts for oxidative allylic C-H functionalization of terminal, di- and trisubstituted olefins will be presented. Mechanistic insights leading to new reaction protocols for regiochemical control, and new catalyst designs that facilitate enantioselective reactions with nitrene amidating reagents will be described. Illustrative examples of emergent applications will be provided.