The Pd-catalyzed dearomatization of chloromethylnaphthalene with allenyltributylstannane has been investigated at the B3LYP density functional level of theory. The calculations indicate that the monophosphine complex is catalytically more active than the bisphosphine complex for oxidative addition. The transmetalation step is a crucial step for determining the dearomatized products due to the formation of two stable bis-蟺-complexes. It is found that reductive elimination occurs by coupling the terminal carbons of the 畏1-propargyl ligand and 畏1-allenyl ligand with the para-carbons of the 畏3-methylnaphthalene ligands in 畏3-methylnaphthalene-畏1-propargyl-Pd(PH3) and 畏3-methylnaphthalene-畏1-allenyl-Pd(PH3) to form the corresponding allenylated and propargylated dearomatization products. For comparison, various C鈥揅 coupling pathways in reductive elimination have also been studied.