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標題: Convenient and efficient Suzuki-Miyaura cross-coupling reactions catalyzed by palladium complexes containing N,N,O-tridentate ligands
作者: Patil, S.A.
Weng, C.M.
Huang, P.C.
Hong, F.E.
關鍵字: N,N,O-Tridentate ligand;Suzuki-Miyaura cross-coupling reaction;Palladium complex;DFT methods;density-functional theory;oxidative addition;stable carbenes;coordination chemistry;nucleophilic-carbene;metal-complexes;aryl;chlorides;mizoroki-heck;hydrazone;mechanism
Project: Tetrahedron
期刊/報告no:: Tetrahedron, Volume 65, Issue 15, Page(s) 2889-2897.
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. (C) 2009 Elsevier Ltd. All rights reserved.
ISSN: 0040-4020
DOI: 10.1016/j.tet.2009.02.017
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