Synthesis of Alkyl Aryl Ethers by O-Arylation of Alcohols with Diaryliodonium Salts: Scope, Limitations, and Mechanism

被引：6

作者：

Gallagher, Rory T. ^{[1
]}

Jha, Soocheta ^{[1
]}

Metze, Bryan E. ^{[1
]}

Stuart, David R. ^{[1
]}

机构：

[1] Portland State Univ, Dept Chem, 1719 SW 10th Ave, Portland, OR 97201 USA

来源：

SYNLETT | 2024年 / 35卷 / 08期

基金：

美国国家科学基金会;

关键词：

arylation; ethers; alcohols; diaryliodonium compounds; ligand coupling; C-O coupling; METAL-FREE ARYLATION; COUPLING REACTIONS; BOND FORMATION; HALIDES; FUNCTIONALIZATION; PHOTOREDOX; SECONDARY; PHENOLS; AMINES;

D O I：

10.1055/a-2198-3637

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe the development of a C-O coupling reaction between aryl(2,4,6-trimethoxyphenyl)iodonium salts and aliphatic alcohols under weak base conditions. The scope of the reaction is presented, with 16 examples ranging in yield from moderate to high (54- 96%). The limitations of the reaction are also presented. Mechanistic experiments reveal a complex network of reactions that include side reactions that generate arynes and oxidize the alcohol nucleophile.

引用

页码：889 / 894

页数：6

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