A catalytic and mechanistic investigation of a PCP pincer palladium complex in the Stille reaction

Abstract

In an improved procedure, the complex {2,6-bis[(diphenylphosphino)methyl]benzene}chloropalladium(II) (1) was synthesised as its THF adduct and the structure was determined by X-ray crystallography. The catalytic properties of the derivative {2,6-bis[(diphenylphosphino)methyl]benzene}(trifluoroacetato)palladium(II) (2) was investigated in the Stille reaction. Complex 2 proves to be an excellent catalyst for the C–C cross-coupling between trimethyl phenyl stannane and aryl bromides using a very low catalyst loading (0.1–0.0001%), giving high turnover numbers (TONs) up to 6.9 × 10⁵. A kinetic investigation of the catalytic reaction suggests a heterogeneous colloidal palladium catalyst formed from the PCP Pd(II) pre-catalyst.