Palladium(0)-catalyzed amination, Stille coupling, and Suzuki coupling of electron-deficient aryl fluorides

被引：163

作者：

Kim, YM ^{[1
]}

Yu, S ^{[1
]}

机构：

[1] Pfizer Global Res & Dev, Chem Res & Dev, La Jolla LAbs, San Diego, CA 92121 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 07期

关键词：

D O I：

10.1021/ja028966t

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The amination of 2-fluoronitrobenzene was Pd(0) catalyzed at 65 °C in DMF, and the effectiveness of the catalysis was ligand-dependent. Among the five catalyst systems investigated, Pd(PPh3)4 was the most effective catalyst. The control experiments revealed that Pd(OAc)2 or PPh3 was not responsible for the catalysis. 4-Fluoro-3-nitro-benzonitrile and 4-fluoro-3-nitro-benzaldehyde also underwent Stille coupling and Suzuki coupling in the presence of Pd(PPh3)4, and the reactions afforded the coupling products in 28-86% yields. The control experiments showed no sign of reaction in the absence of palladium. These results were in agreement with the oxidative addition/reductive elimination pathway, where the oxidative addition could conceivably proceed via the SNAr mechanism. Copyright © 2003 American Chemical Society.

引用

页码：1696 / 1697

页数：2

共 16 条

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