Regio- and Chemoselective Metalation of Arenes and Heteroarenes Using Hindered Metal Amide Bases

被引：336

作者：

Haag, Benjamin ^{[1
]}

Mosrin, Marc ^{[1
]}

Ila, Hiriyakkanavar ^{[2
]}

Malakhov, Vladimir ^{[1
]}

Knochel, Paul ^{[1
]}

机构：

[1] Univ Munich, Dept Chem, D-81377 Munich, Germany

[2] Jawaharlal Nehru Ctr Adv Sci Res, New Chem Unit, Bangalore 560064, Karnataka, India

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 42期

基金：

欧洲研究理事会;

关键词：

magnesium; metal amides; metalation; synthetic methods; zinc; DIRECTED ORTHO-METALATION; CROSS-COUPLING REACTIONS; CENTER-DOT-LICL; CATALYZED ASYMMETRIC CARBOALUMINATION; COMPLEXED HETEROATOM CARBANIONS; ARYL MAGNESIUM REAGENTS; FRUSTRATED LEWIS PAIRS; MIXED LITHIUM-CADMIUM; CARBON BOND FORMATION; POLYFUNCTIONAL ARYL;

D O I：

10.1002/anie.201101960

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The preparation of highly functionalized organometallic compounds can be achieved by direct C-H activation of a broad range of unsaturated substrates using lithium chloride solubilized 2,2,6,6-tetramethylpiperidide bases (TMP nMXm·p LiCl). These are excellent reagents for converting a wide range of aromatic and heterocyclic substrates into valuable organometallic reagents with broad applications in organic synthesis. Valuable synthetic intermediates can be obtained by quenching with various electrophiles highly functionalized aryl-, heteroaryl-, and alkenylmetal compounds prepared by direct C-H activation using lithium chloride solubilized 2,2,6,6- tetramethylpiperidide bases, such as TMPMgCl·LiCl, TMPZnCl·LiCl, or TMP2Zn·2 LiCl, which tolerate a wide range of functional groups. The scope and limitations are given for each LiCl-solubilized base. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：9794 / 9824

页数：31

共 427 条

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