Firsts lysidinyl- and lysidinium-triphosphines Pd(II) complexes

The preparation of the first lysidinyl- (or imidazolin-1-yl-) triphosphine and its coordination to palladium complexes are described, as well as the related alkylated derivatives of the latter. The preparation of first lysidinyl-triphosphine ligand (named Triphosline) is described in three steps which are first a Michael type addition of imidazolidine (or lysidine) to diethylvinylphosphonate, second a phosphonate reduction with LiAlH 4 and third an anti-Markovnikov radical addition of the primary phosphine to diphenylvinylphosphine. The Triphosline behaves as a tridentate P-coordinating ligand in palladium(II) complexes. The dangling lysidine function is then cleanly and totally alkylated by methyl iodide to lead to a new kind of lysidinium-triphosphine complexes. Subsequent anion exchange with TlPF 6 affords the first example of a chloride free lysidinium-triphosphine palladium complex which has been fully characterized by spectroscopic and analytical methods.