The curiosity surrounding tosyl allenols lies in their potential to unlock novel reactivity modes through synergistic transition metal catalysis and red-light activation—offering mild, sustainable pathways to architecturally complex molecules.  A particularly notable aspect of tosyl allenol, which serves as a dual-functional handle, is its capacity to participate in intricate, multi-pathway reactivity. The orthogonal π-systems inherent to the allene structure are recognized for their unique interactions with transition metals, which promote regio- and stereoselective bond formation. Concurrently, the electron-withdrawing tosyl group may modulate the electronic properties of the molecule, affecting reaction pathways in both unpredictable and tunable manners. In light of these considerations, our primary objective is to synthesize a targeted library of tosyl allenol derivatives and to analyze their reactivity profiles under transition-metal-catalyzed conditions, as well as through a red-light-driven sustainable synthetic approach. We aim to enhance atom economy, stereoselectivity, scalability, and overall yields within our synthetic processes. Specifically, our efforts focus on the strategic synthesis of structurally significant and synthetically valuable organic scaffolds, including bicyclics, polycycles, and heterocycles, while also characterizing their biological or material-relevant properties. Furthermore, we plan to explore their potential applications for bioimaging targeted at specific cell organelles.