Mechanistic Insight into the Nickel-Catalyzed Cross-Coupling of Aryl Phosphates with Arylboronic Acids: Potassium Phosphate is Not a Spectator Base but is Involved in the Transmetalation Step in the Suzuki–Miyaura ReactionSubmitted by Jun Zhu on Fri, 11/01/2013 - 11:44
Spectator or actor? Density functional theory calculations were performed to examine the role of the base in the nickel-catalyzed cross-coupling of aryl phosphates with arylboronic acids. Potassium phosphate was found to not act as a spectator base but was involved in the transmetalation step, as shown by a lower barrier than that of a base-free process, owing to the activation of the carbonboron bond by the base. Further experimental observations support the theoretical findings.