 A series of easily prepared, phosphine-ligated palladium (II) precatalysts based on the 2-aminobiphenyl scaffold have been synthesized. The role of the palladium-associated halide or pseudohalide in the formation and stability of the palladacycle has been examined. It was found that replacing the chloride in the previous version of the precatalyst with methanesulfonate leads to a new class of precatalysts. These new precatalysts exhibit greatly improved solution stability and are readily prepared from a much wider range of phosphine ligands. They have been found to incorporate extremely bulky biaryl ligands previously impossible to incorporate into palladium precatalysts. Structural differences in the solid state between the previous version of precatalyst and the palladium methanesulfonate precatalysts have been explored. In addition, the reactivity of the latter is examined in a range of C�C, C-O, and C�N bond forming reactions.

Design of palladium (II) methanesulfonate precatalysts for C-C, C-O and C-N cross-coupling reactions

246th National Meeting (2013)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.