Our laboratory, with a focus on developing efficient and selective tools for carbohydrate modification, has recently established a 1,2-radical migration (RaM) strategy for selective C2functionalization of carbohydrates. 17 Building on this foundation, we proposed leveraging this 1,2-RaM reactivity in tandem with excited-state Pd-catalyzed radical allylic alkylation of alkenes. This synergistic approach aims to streamline the synthesis of C2-allylated sugars from readily available 1-bromosugars (Figure ), enabling a novel intermolecular Heck-type crosscoupling mechanism for the selective formation of allylation products. We envisioned the excited-state palladium catalyst reacting with 1-bromosugar to generate C1-radical, which undergoes 1,2-RaM to afford C2-radical. The addition of this radical intermediate to 1,1-disubstituted alkenes, followed by selective hydride loss, liberates the desired C2-allyl sugar. However, to realize the desired reaction, we must address the following challenges: (i) achieving kinetic control over the 1,2-RaM and radical allylation to favor C2-allylation and (ii) directing -hydride elimination from the palladium-alkyl species to favor terminal (allylic sugar) over internal (vinylic sugar) products. If successful, this strategy will broaden the application scope of excited-state Pd catalysis and provide a more direct and versatile pathway for rapid access to C2-allyl sugars, addressing a significant challenge in carbohydrate chemistry.