This dissertation details recent developments in palladium catalyzed carbon-carbon bond formation reactions with two areas of focus: the palladium catalyzed branched and enantioselective allyl-allyl cross-coupling, and the palladium catalyzed carbonylative conjugate addition. Allyl-allyl cross-coupling presents an opportunity to synthesize 1,5-dienes, a scaffold that resembles subunits of terpenes, a critical building block in nature. Chapter I provides an overview of the developments in the allyl-allyl cross-coupling area. Chapter II, III, and IV detail strategies to construct complex substituted asymmetric 1,5-dienes through branched selective and enantioselective allyl-allyl cross-coupling. In chapter V, the palladium catalyzed carbonylative conjugate addition is discussed. This method enables the synthesis of 1,4-dicarbonyl compounds in an atom economical and environmentally friendly fashion, and provides a direct access to five membered heterocycles, a valuable class of chemicals in medicine.