Palladium catalyzed reductive homocoupling reactions of aromatic halides in dimethyl sulfoxide (DMSO) solution

被引：61

作者：

Qi, Chenze ^{[1
]}

Sun, Xudong ^{[1
]}

Lu, Cuiyun ^{[1
]}

Yang, Jinzhi ^{[1
]}

Du, Yijun ^{[1
]}

Wu, Huajiang ^{[1
]}

Zhang, Xian-Man ^{[1
]}

机构：

[1] Shaoxing Univ, Dept Chem, Shaoxing 312000, Zhejiang, Peoples R China

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2009年 / 694卷 / 18期

关键词：

Palladium catalyst; Homocoupling; Aromatic halides; Alkali fluoride bases; X-ray photoelectron spectroscopy; Reaction mechanism; CROSS-COUPLING REACTIONS; ARYL HALIDES; SYMMETRICAL BIARYLS; ULLMANN REACTION; MOLECULAR-HYDROGEN; BOND FORMATION; COMPLEXES; FLUORIDE; MECHANISM; EFFICIENT;

D O I：

10.1016/j.jorganchem.2009.04.021

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Biaryls were obtained in good to excellent yields from the palladium catalyzed reductive homocoupling reactions of various aryl iodides and bromides in dimethyl sulfoxide (DMSO) solution without the need for any additional reducing reagents. Pd(dppf)Cl(2) is the most effective among the screened palladium catalysts for the homocoupling reactions. Fluorides, carbonates, acetates and hydroxides can be used as bases at promoting the palladium catalyzed reductive homocoupling of aryl halides in DMSO solution. X-ray photoelectron spectroscopic (XPS) analysis shows that the oxidative Pd(2+)(dppf) species can be reduced into the Pd(0)(dppf) active species by solvent DMSO molecules to furnish the catalytic cycle, indicating that DMSO plays a dual role as both solvent and reducing reagent. A plausible reaction mechanism has been discussed. Elimination of additional reducing reagents will not only reduce the reaction operation cost, but will also simplify the product separation and purification. (C) 2009 Elsevier B.V. All rights reserved.

引用

页码：2912 / 2916

页数：5

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