Tuning Reactivity and Site Selectivity of Simple Arenes in C-H Activation: Ortho-Arylation of Anisoles via Arene-Metal π-Complexation

被引：46

作者：

Ricci, Paolo ^{[1
,2
]}

Kraemer, Katrina ^{[1
]}

Larrosa, Igor ^{[2
]}

机构：

[1] Queen Mary Univ London, Sch Biol & Chem Sci, London E1 4NS, England

[2] Univ Manchester, Sch Chem, Oxford M13 9PL, England

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2014年 / 136卷 / 52期

基金：

英国工程与自然科学研究理事会; 欧洲研究理事会;

关键词：

CATALYZED DIRECT ARYLATION; CARBOXYLIC-ACIDS; BOND ACTIVATION; FUNCTIONALIZATION; POLYFLUOROARENES; COUPLINGS; BENZENE; BIARYLS;

D O I：

10.1021/ja510260j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Current approaches to achieve site selectivity in the CH activation of arenes involve the use of directing groups or highly electron-poor arenes. In contrast, simple arenes, such as anisole, are characterized by poor reactivity and selectivity. We report that pi-complexation to a Cr(CO)(3) unit enhances the reactivity of anisoles providing an unprecedented ortho-selective arylation. This mild methodology can be used for the late stage functionalization of bioactive compounds containing the anisole motif, allowing the construction of novel organic scaffolds with few synthetic steps.

引用

页码：18082 / 18086

页数：5

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