Mechanistic studies of palladium catalyzed cross-coupling reactions and predictions with theoretical methods

Abstract

The 2010 Noble prize in chemistry awarded to Prof. Richard F. Heck, Prof. Ei-ichi Negeishi, and Prof. Akira Suzuki for their contribution to the development of Pd-catalyzed C–C cross-coupling reaction represents the power and importance of Pd-catalyzed cross-coupling reactions. While the method was improved with the finding of new nucleophilic coupling partners like organoborane and zinc at the beginning, the development of a new catalyst based on the mechanistic understandings further expands the substrate scope and improves the reactivity, making it an essential tool for synthetic chemists. In this thesis, we investigated the mechanism of Pd-catalyzed cross-coupling reaction, especially using dialkyl biaryl monophosphine as a ligand, by employing density functional theory based calculation. This study sheds light on not only the detailed mechanism of the cross-coupling reactions but also shows the availability of the reactivity prediction with computational methods and suggests some strategies for efficient catalyst development.