LAUSR

Abstract Condensation reaction of 2-naphthaldehyde with one equivalent of benzohydrazide in presence of acetic acid in refluxing methanol yielded the Schiff base N' -(2-naphthylidene)benzohydrazide (H 2 L) in 86% yield. Reaction of equimolar amounts of Li 2 PdCl 4 (generated in situ from PdCl 2 and LiCl taken in 1:2 mol ratio), H 2 L and NaOAc·3H 2 O in methanol at room temperature provided the complex [Pd(HL)Cl] ( 1 ) in 82% yield. Treatment of 1 mol equivalent of 1 with 2 mol equivalents of PPh 3 in acetone at room temperature produced the complex [Pd(L)(PPh 3 )] ( 2 ) in 72% yield. The Schiff base and the two complexes were characterized by elemental analysis, mass spectrometric and various spectroscopic (IR, UV–Vis and 1 H NMR) measurements. The molecular structures of both complexes ( 1 and 2 ) were determined by single crystal X-ray crystallography. In each square-planar complex, the tridentate ligand (HL − in 1 and L 2− in 2 ) acts as pincer-like CNO-donor. The fourth coordination site is occupied by chloride in 1 , while that in 2 is satisfied by the P-atom of PPh 3 . The 2-naphthyl fragment of both HL − and L 2− is palladated at the 3-position. Complex 2 was found to be an effective catalyst for one-pot Suzuki-Miyaura double cross-coupling reactions of 3,5-dihalosalicylaldehydes with a variety of arylboronic acids to provide the corresponding triaryl products in moderate to excellent yields.