Experimental and theoretical studies on the oxidative addition of palladium(0) to β-chlorovinamidinium salts

Boronic acids, esters and borinic anhydrides are partners in Suzuki–Miyaura cross-coupling reactions with a variety of β-chlorovinamidinium salts to give the desired β-arylvinamidinium salts in up to 88% yield. Reduction is a competing reaction pathway. DFT calculations on the intermediate palladium complex reveal that the Pd–C interaction is predominantly of σ-symmetry and the metal based LUMO is mainly dz2 in character.