New Directions in the Development of Water-Soluble Phosphines and Transition Metal Compounds

The water-soluble bisphosphines, 1,2-bis(bis(hydroxymethyl)phosphino)benzene ("HMPB") (1) and 1,2-bis(bis(hydroxymethyl)phosphino)ethane ("HMPE") (2) were synthesized in near quantitative yields by the catalytic hydroformylation of H 2 PC 6 H 4 PH 2 and H 2 PCH 2 CH 2 PH 2 in the presence of formaldehyde in aqueous media. 1.2 The reactions of these chelating bisphosphines 1 and 2 with Pt(COD)Cl 2 and Pd(PhCN) 2 Cl 2 produced water-soluble Pt(II) and Pd(II) complexes M[(HOH 2 C) 2 PC 6 H 4 P(CH 2 OH) 2 ] 2 Cl 2 (M = Pt, 3; Pd, 4) and M[(HOH 2 C) 2 PCH 2 CH 2 P(CH 2 OH) 2 ] 2 Cl 2 (M = Pt, 5; Pd, 6) respectively. The reactions of 1 and 2 with Re(O 2 )I(Ph 3 ) 2 and Re(O) 2 (NHC 5 H 5 ) 4 ]Cl to produce new water-soluble Re(V) complexes are also described. All the new compounds were characterized by 1 H and 31 P NMR spectroscopy. X-ray structures of representative Pd(II) and Re(V) complexes as shown below confirmed the chemical constitution of this new generation of water-soluble metal complexes.