Palladium salicylaldimine complexes derived from 2,3-dihydroxybenzaldehyde

Schiff bases derived from condensation of 2,3-dihydroxybenzaldehyde with various primary amines, such as 1-adamantanamine hydrochloride, 2,6-dimethylaniline, 2,6-diethylaniline and 2,6-diisopropylaniline, react with palladium(II) acetate to give the corresponding bis(N-arylsalicylaldiminato)palladium(II) complexes. These complexes have been found to be active catalyst precursors for the Suzuki–Miyaura cross-coupling of aryl bromides and iodides with aryl boronic acids using water as a solvent.

Reactions of 2,3-dihydroxybenzaldehyde with various primary amines have been examined. Addition of these Schiff base ligands to Pd(II) salts afforded bis(N-arylsalicylaldiminato)palladium complexes. New palladium compounds have been examined for their potential catalytic activity for Suzuki–Miyaura cross-coupling reactions in water.Figure optionsDownload as PowerPoint slideHighlights
► Synthesis of salicylaldimines derived from 2,3-dihydroxybenzaldehyde.
► Molecular structures of three salicylaldimines are presented.
► Coordination of these salicylaldimines to palladium(II) gives active cross-coupling pre-catalysts in water.