The selective reaction of aryl halides with KOH: Synthesis of phenols, aromatic ethers, and benzofurans

被引：443

作者：

Anderson, Kevin W. ^{[1
]}

Ikawa, Takashi ^{[1
]}

Tundel, Rachel E. ^{[1
]}

Buchwald, Stephen L. ^{[1
]}

机构：

[1] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 33期

关键词：

D O I：

10.1021/ja0639719

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The direct and selective synthesis of phenols from aryl/heteroaryl halides and KOH has been achieved through the use of highly active monophosphine-based catalysts derived from Pd2dba3 and ligands L1 or L2 and the biphasic solvent system 1,4-dioxane/H2O. We have also demonstrated a one-pot method of phenol formation/alkylation for the preparation of alkyl aryl ethers from aryl halides. In many instances, this protocol overcomes limitations in existing Pd-catalyzed coupling reactions of aliphatic alcohols with aryl halides. Finally, we demonstrate that substituted benzofurans can be prepared efficiently via a Pd-catalyzed phenol formation/cyclization protocol starting from 2-chloroaryl alkynes. Copyright © 2006 American Chemical Society.

引用

页码：10694 / 10695

页数：2

共 16 条

[1] General and efficient indole syntheses based on catalytic amination reactions [J].