Despite their relative stability, alkynes can form equilibrium mixtures with their formal tautomers, allenes (Figure , top). Alkyne-allene isomerization typically requires a strong base under harsh conditions. However, this process can also occur under milder conditions with a weak base if the acidity of protons neighboring the triple bond is enhanced, for instance, by the presence of a proximal electron-withdrawing group (EWG). This leads to the formation of an EWG-conjugated allene which possesses a different reactivity than the original, non-conjugated alkyne. Drawing from the in situ alkyne-allene isomerization facilitating cycloaddition reactions, we propose employing this process as an activation step in an envisioned TM-free hydrocyanation of alkynes. Consequently, EWG-activated allenes represent a reactive species in the conjugated addition of various nucleophiles. For example, recently, Lee et al. demonstrated a catalytic system that allowed for the addition of secondary phosphine oxides to allenoates with remarkable regioselectivity (Figure , bottom). Given the relative similarity in the electronic effects of CN moiety and Lewis acidcoordinated P(O)R2 group, we postulate that such a process may be feasible for HCN addition (Figure , bottom).