Several
chitosan and 6-deoxy-6-amino
chitosan-Schiff base ligands (1
x2013;4) were prepared by condensation of either 2-pyridinecarboxaldehyde or 2-(diphenylphosphino)benzaldehyde with the amino group(s) on
chitosan and its derivative (6-deoxy-6-amino
chitosan). The supported ligands were reacted with [PdCl
2(COD)] to form
chitosan-supported Pd
II catalysts (5
x2013;8). All the supported catalysts were air- and moisture-stable and have been characterized using elemental analysis, ICP-MS, UV
x2013;vis, FT-IR, PXRD, TGA,
31P solid state NMR and TEM. As models for the heterogenized catalysts (5 and 6), mononuclear Pd
II complexes (9 and 10) were also prepared via the Schiff-base condensation reaction of 1,3,4,6-tetra-O-acetyl-β-d-glucosamine hydrochloride to form 1,3,4,6-tetra-O-acetyl-β-d-glucos-2-pyridylimine and 1,3,4,6-tetra-O-acetyl-β-d-glucos-2-(diphenylphosphino)imine which were subsequently reacted with [PdCl
2(COD)]. Complexes (9 and 10) and their precursors were characterized by
1H and
31P NMR, UV
x2013;vis, FT-IR spectroscopy and elemental analysis.
Catalytic Suzukix2013;Miyaura and Heck carbonx2013;carbon cross-coupling reactions were carried out using the supported Pd catalysts and their mononuclear analogues. The immobilized and homogeneous catalysts showed high activity for both the Suzukix2013;Miyaura and Heck cross-coupling reactions in organic and aqueous media. Homogeneous catalysts (9 and 10) decomposed during the first run, while the supported catalysts could be recycled and reused up to five times.