A General Strategy Toward Aromatic 1,2-Ambiphilic Synthons: Palladium-Catalyzed ortho-Halogenation of PyDipSi-Arenes

被引：97

作者：

Dudnik, Alexander S. ^{[1
]}

Chernyak, Natalia ^{[1
]}

Huang, Chunhui ^{[1
]}

Gevorgyan, Vladimir ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2010年 / 49卷 / 46期

关键词：

benzynes; C-H activation; halogenation; palladium; siloles; DIVERSITY-ORIENTED SYNTHESIS; DIRECTED ORTHO-METALATION; CROSS-COUPLING REACTION; ARYLBORONIC ACIDS; ARYL; HALIDES; IODINATION; BORYLATION; ACTIVATION; ARYLATION;

D O I：

10.1002/anie.201004426

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A general and efficient strategy to synthesize 1,2-ambiphilic aromatic and heteroaromatic synthons from haloarenes has been developed. The method involves installation of the PyDipSi directing group, and subsequent palladium-catalyzed directed ortho-halogenation of aryl silanes (see scheme; Py=2-pyridyl). The usefulness of these 1,2-ambiphilic building blocks was shown in their participation as both nucleophilic aryl silane and electrophilic aryl iodide moieties. © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：8729 / 8732

页数：4

共 53 条

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