The deprotection of phosphonium chloride salts [PR₂(CH₂OH)₂]⁺Cl⁻ and subsequent condensation reaction with N-methyl-2-aminopyridine has been carried out to give a series of ligands of the form PR₂CH₂N(CH₃)C₅H₄N (R = Ph 6, Cy 7, t-Bu 8) which have been fully characterised either as the pure ligand (6) or the air stable borane adducts (R = Cy 7a, t-Bu 8a). The 1 : 1 reactions of 6, 7 and 8 with PdCl₂(COD) gave the N,P chelate complexes [Pd{PR₂CH₂N(CH₃)C₅H₄N}Cl₂]; the Cy (10) and t-Bu (11) complexes were characterised by X-ray crystallography. The bisligated species [Pd{PCy₂CH₂N(CH₃)C₅H₄N}₂Cl₂] (12) was obtained when the reaction was carried out at higher temperatures and the ligands were found to be coordinated to the metal in a trans configuration through the phosphorus donors. Abstraction of the chlorides from the bis-ligated species 12, using silver salts, resulted in the coordination of the pyridine ring forming the bis-chelate complex [Pd{PCy₂CH₂N(CH₃)C₅H₄N}₂]²⁺13. In comparison, the palladium bis-chelate complex of ligand 5 [Pd{PPh₂CH₂N(CH₃)C₅H₄N}₂]²⁺ (14) was shown to form in a cis configuration and was fully characterised by X-ray crystallography.