Computational study of the transmetalation process in the Suzuki-Miyaura cross-coupling of aryls

The transmetalation step of the Suzuki-Miyaura cross-coupling between aryl groups is analyzed by means of DFT calculations with the Becke3LYP functional. The halide considered is Ph-Br, and the organoboronic acid is Ph-B(OH)(2). The model catalyst is Pd(PH3)(2), and the base, OH-. The transmetalation is considered to start from the Pd(Ph)(PH3)(2)Br complex, the product of the oxidative addition. The results are compared with those of a previous study on the analogous reaction with vinyl groups, and it is shown that the reaction mechanism is very similar. (c) 2006 Elsevier B.V. All rights reserved.