Convenient and efficient Suzuki-Miyaura cross-coupling reactions catalyzed by palladium complexes containing N,N,O-tridentate ligands |
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Authors: | Siddappa A Patil |
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Institution: | Department of Chemistry, National Chung Hsing University, Taichung 40227, Taiwan |
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Abstract: | N,N,O-Tridentate ligands 1-9 were prepared from the condensation of amines with nine aromatic aldehydes or ketones. These ligands are thermally stable and neither air- nor moisture-sensitive. Combination of either 2-methoxy-6-(pyridine-2-ylmethylimino)-methyl]-phenol, 1 or 2-(benzothiazol-2-yl-hydrazonomethyl)-4,6-di-tert-butyl-phenol, 6 with Pd(OAc)2 furnished an excellent catalyst precursor for the Suzuki-Miyaura cross-coupling of various aryl bromides with arylboronic acids. The effects of varying solvents, bases, and ligand/palladium ratios on the performance of the coupling reaction were investigated. The molecular structures of both free ligand 1 and its palladium acetate complex 10 were determined by single-crystal X-ray diffraction methods. The DFT studies revealed that the catalytic performance of palladium complexes involving this type of a ligand may differ greatly upon a small variation in its structure. |
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Keywords: | N N O-Tridentate ligand Suzuki-Miyaura cross-coupling reaction Palladium complex DFT methods |
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