Convenient and efficient Suzuki-Miyaura cross-coupling reactions catalyzed by palladium complexes containing N,N,O-tridentate ligands

被引：55

作者：

Patil, Siddappa A. ^{[1
]}

Weng, Chia-Ming ^{[1
]}

Huang, Po-Cheng ^{[1
]}

Hong, Fung-E ^{[1
]}

机构：

[1] Natl Chung Hsing Univ, Dept Chem, Taichung 40227, Taiwan

来源：

TETRAHEDRON | 2009年 / 65卷 / 15期

关键词：

N; O-Tridentate ligand; Suzuki-Miyaura cross-coupling reaction; Palladium complex; DFT methods; OXIDATIVE ADDITION; COORDINATION CHEMISTRY; NUCLEOPHILIC-CARBENE; METAL-COMPLEXES; ARYL CHLORIDES; MIZOROKI-HECK; HYDRAZONE; MECHANISM; THERMOCHEMISTRY; AMINATION;

D O I：

10.1016/j.tet.2009.02.017

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：2889 / 2897

页数：9

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