Transition metal-catalyzed dipolar cycloaddition is one of the most efficient and powerful synthetic strategies to produce diverse heterocycles. In particular, for the construction of oxygen-containing heterocycles, which are valuable structural motifs found in pharmaceuticals and natural compounds, transition metal-catalyzed oxa-dipolar cycloaddition using an oxygen-containing dipole has emerged as a promising method. In recent years, the 1,4-O/C dipole synthons 2-alkylidenetrimethylene carbonate and 2-hydroxymethylallyl carbonate have been developed and successfully applied to palladium-catalyzed oxa-[4 + n] dipolar cycloadditions with diverse dipolarophiles. In this review, we summarize recent advances in palladium-catalyzed oxa-[4 + n] dipolar cycloadditions using 1,4-O/C dipoles including asymmetric catalysis and divergent catalysis toward five- to nine-membered O-heterocycles.