This review discusses transition metal-catalyzed decarboxylative allylation and benzylation reactions, highlighting their importance in generating nucleophilic species through decarboxylation. Decarboxylative coupling offers advantages over traditional cross-coupling methods, such as using inexpensive substrates, mild conditions, and environmentally benign byproducts. The review covers the development of homogeneous catalysis for these reactions, emphasizing the generation of enolates via decarboxylation and their subsequent coupling. It discusses various mechanisms, substrates, and catalysts, including palladium, molybdenum, nickel, and rhodium, and explores regioselectivity, stereoselectivity, and asymmetric DcA reactions. The review also addresses the challenges and solutions in achieving high enantioselectivity and diastereoselectivity, as well as the role of different ligands and protecting groups in controlling reaction outcomes. The study highlights the versatility of decarboxylative allylation in synthesizing complex molecules with high stereochemical control.This review discusses transition metal-catalyzed decarboxylative allylation and benzylation reactions, highlighting their importance in generating nucleophilic species through decarboxylation. Decarboxylative coupling offers advantages over traditional cross-coupling methods, such as using inexpensive substrates, mild conditions, and environmentally benign byproducts. The review covers the development of homogeneous catalysis for these reactions, emphasizing the generation of enolates via decarboxylation and their subsequent coupling. It discusses various mechanisms, substrates, and catalysts, including palladium, molybdenum, nickel, and rhodium, and explores regioselectivity, stereoselectivity, and asymmetric DcA reactions. The review also addresses the challenges and solutions in achieving high enantioselectivity and diastereoselectivity, as well as the role of different ligands and protecting groups in controlling reaction outcomes. The study highlights the versatility of decarboxylative allylation in synthesizing complex molecules with high stereochemical control.