Gold(I) Complexes with Ferrocenylphosphino Sulfonate Ligands: Synthesis and Application in the Catalytic Addition of Carboxylic Acids to Internal Alkynes in Water

The synthesis and characterization of novel gold(I) complexes containing hydrophilic ferrocenylphosphino sulfonate ligands, i.e., compounds [AuCl{(eta(5)-C5H3PR2((SO3Pr)-Pr-i))Fe(eta(5)-C5H5)}] (R = Ph (2a), p-Tol (2b), Cy (2c)), are presented, including a single-crystal X-ray diffraction study on 2a. Complexes 2a-c were checked as catalysts for the intermolecular addition of carboxylic acids to nonactivated internal alkynes using water as a green reaction medium. The best results in terms of activity were obtained with 2a in combination with AgOAc, which was able to promote the selective anti addition of a variety of aromatic, aliphatic, and alpha,beta-unsaturated carboxylic acids to both symmetrical and unsymmetrical internal alkynes at 60 degrees C, employing metal loadings of only 2 mol %.