We continue our investigations into dual catalytic alkene functionalization promoted by a metal and a transient directing group (TDG). We previously described methods for Heck-type hydroarylation and 1,2-arylfluorination. In this ChemRxiv pre-print we show that it is instead possible to achieve C(alkenyl)–H activation from a common Pd(II)–alkene olefin intermediate, as promoted by a tailored carboxylate additive. This mode of reactivity can be leveraged in the oxidative cross-coupling of two alkenes to yield 1,3-diene products, including axially chiral 3-aryl-1,3-dienes. Congrats to the entire project team: Mingyu, Juntao, Hui-Qi, and Raúl from our lab; and Tuğçe from the Liu group the University of Pittsburgh.