Direct α-Arylation of Ethers through the Combination of Photoredox-Mediated C-H Functionalization and the Minisci Reaction

被引：399
|
作者：
Jin, Jian [1 ]
MacMillan, David W. C. [1 ]
机构：
[1] Princeton Univ, Merck Ctr Catalysis, Princeton, NJ 08544 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 05期
关键词：
alkylation; C-H functionalization; ethers; heterocycles; photoredox catalysis; FREE-RADICAL REACTIONS; NUCLEOPHILIC CHARACTER; ALKYL RADICALS; HETEROAROMATIC BASES; RATE CONSTANTS; SINGLE-LAYER; LIGHT; CATALYSIS; PHOTOCHEMISTRY; PHOTOPHYSICS;
D O I：
10.1002/anie.201410432
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The direct alpha-arylation of cyclic and acyclic ethers with heteroarenes has been accomplished through the design of a photoredox-mediated C-H functionalization pathway. Transiently generated alpha-oxyalkyl radicals, produced from a variety of widely available ethers through hydrogen atom transfer (HAT), were coupled with a range of electron-deficient heteroarenes in a Minisci-type mechanism. This mild, visible-light- driven protocol allows direct access to medicinal pharmacophores of broad utility using feedstock substrates and a commercial photocatalyst.
引用
收藏
页码：1565 / 1569
页数：5
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