An organic dye photocatalyzed lactonization-alkynylation of easily accessible homoallylic cesium oxalates using ethynylbenziodoxolones (EBXs) reagents has been developed. The reaction gave access to valuable functionalized lactones and lactams in up to 88% yield via the formation of two new C-C bonds. The transformation was carried out on primary, secondary and tertiary homoallylic alcohols and primary homoallylic amines and could be applied to the synthesis of spirocyclic compounds, as well as fused and bridged bicyclic lactones.