Pd/C as a Catalyst for Completely Regioselective C-H Functionalization of Thiophenes under Mild Conditions

被引：165

作者：

Tang, Dan-Tam D. ^{[1
]}

Collins, Karl D. ^{[1
]}

Ernst, Johannes B. ^{[1
]}

Glorius, Frank ^{[1
]}

机构：

[1] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 07期

关键词：

C-H functionalization; heterogeneous catalysis; hypervalent iodine compounds; Pd; C; thiophenes; DIRECT ARYLATION; BOND FUNCTIONALIZATIONS; HETEROGENEOUS CATALYSIS; ASYMMETRIC CATALYSIS; COUPLING REACTIONS; ROBUSTNESS SCREEN; ARYLBORONIC ACIDS; NATURAL-PRODUCTS; RAPID ASSESSMENT; NANOPARTICLES;

D O I：

10.1002/anie.201309305

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The completely C3-selective arylation of thiophenes and benzo[b]thiophenes was achieved by using Pd/C as a heterogeneous catalyst without ligands or additives under mild reaction conditions. The practicability of this transformation is demonstrated by notable functional group tolerance and the insensitivity of the reaction to H2O and air. This method is also applicable to nitrogen- and oxygen-containing heterocycles, yielding the corresponding C2-arylated products. Three-phase tests along with Hg-poisoning and hot-filtration tests suggest that the catalytically active species is heterogeneous in nature.

引用

页码：1809 / 1813

页数：5

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