3,3′-((Arylmethylene)bis(4-methoxy-3,1-phenylene)) dipyridine derivatives as convenient ligands for Suzuki-Miyaura chemo- and homoselective cross-coupling reactions

Four novel N,N-bidentate triarylmethane-based ligands bearing beta-pyridyl residues have been prepared and the catalytic activity of their in-situ generated palladium complexes were studied in the Suzuki-Miyaura cross-coupling reactions. Air and moisture stable 3,3'-((arylmethylene)bis(4-methoxy-3,1-phenylene))dipyridines L1-3 showed excellent activity in the Suzuki coupling reactions of aryl halides with aryl boronic acids under thermal and sonochemical reaction conditions. The described methodology provided good to high yields in short reaction times at ambient conditions. Moreover, it offered a straightforward way for Suzuki-Miyaura chemo- and homoselective cross-coupling of aryl halides with phenyl boronic acid. The structures of synthesized compounds were fully characterized by FT-IR, H-1-NMR, C-13-NMR, and elemental analyses. The coordination of palladium acetate to nitrogen sites of L1 was also studied using FTIR spectroscopy, EDX analysis and SEM observations.

Automated summary

The catalytic activity of four novel N,N-bidentate triarylmethane-based ligands with beta-pyridyl residues in Suzuki-Miyaura cross-coupling reactions was studied, showing excellent activity under thermal and sonochemical reaction conditions. The methodology provided a straightforward way for chemo- and homoselective cross-coupling reactions, with the structures of synthesized compounds fully characterized and studied for their coordination with palladium acetate.