Schiff bases of 1′-hydroxy-2′-acetonaphthone (HAN) containing chalcogen functionalities, 1-HO–C 10 H 6 -2-CH 3 )CN–(CH 2 ) n EC 6 H 4 -4-R (R=H or OMe; n=2 or 3; E=S (L 1 –L 2 ), Se (L 3 –L 4 ) or Te (L 5 –L 6 )) have been synthesized in yield 90–95%. They show characteristic 1 H, 13 C{ 1 H} 77 Se{ 1 H} and 125 Te{ 1 H} (in case of selenated and tellurated species, respectively) NMR spectra. Their complexation with Pd(II), Pt(II), Hg(II) and (p-cymene)Ru(II) has been explored. The single-crystal structures of ligands L 1 , L 3 and L 6 and complexes of Pd(II) with L 1 , L 2 , L 3 and L 5 have been determined. The geometry of Pd is close to square planar in all the complexes and the ligands coordinate in a uni-negative tridentate mode. The Pd–N bond lengths are in the range 1.996(7)–2.019(5)Ǻ. The Pd–Se bond distance is 2.3600(5)Ǻ whereas Pd–Te is 2.5025(7)Ǻ. The Pd(II) complexes of L 1 –L 5 have been found promising as homogeneous catalyst for Heck and Suzuki reactions. The yields obtained were up to 85%.