New chiral ferrocenylamine sulfide and selenide ligands: preparation, characterization and their palladium and platinum complexes as catalysts for selective hydrogenation

Abstract

A series of new ferrocenylamine sulfides and selenides, ( R, S)-(C 5H 3-1-CHMeNMe 2-2-ER)Fe(C 5H 4ER), (E = S; R = Me, Ph, Bz, 4-tolyl and 4-chlorophenyl and E = Se; R = Ph and 4-chlorophenyl) have been prepared by the lithiation of ( R)- N,N-dimethyl-1-ferrocenylethylamine, first in the presence of ether and then TMEDA followed by reaction with the appropriate disulfides or diselenides. These compounds react with (PhCN) 2MCl 2, M  Pd, Pt to form new heterobimetallic complexes, ( R, S)-(C 5H 4-ER)Fe(C 5H 3-1-CHMeNMe 2-2-ER)MCl 2, (E = S, Se; R = Me, Et, n-Pr, i-Pr [1], Ph, Bz, 4-tolyl and 4-chlorophenyl; M = Pd, Pt). The following techniques were used for characterization: 1H and 13C NMR, IR, MS and elemental analysis. The possible structure for the bimetallic complexes is discussed. The palladium ferrocenyl complexes are effective catalysts for selective hydrogenation of dienes to monoenes under homogeneous conditions.