Direct Zincation of Functionalized Aromatics and Heterocycles by Using a Magnesium Base in the Presence of ZnCl2

被引：76

作者：

Dong, Zhibing ^{[1
,2
]}

Clososki, Giuliano C. ^{[3
]}

Wunderlich, Stefan H. ^{[1
]}

Unsinn, Andreas ^{[1
]}

Li, Jinshan ^{[2
]}

Knochel, Paul ^{[1
]}

机构：

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

[2] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

[3] Univ Sao Paulo, Fac Ciencias Farmaceut Ribeirao Preto, BR-14040903 Ribeirao Preto, SP, Brazil

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2009年 / 15卷 / 02期

关键词：

cross-coupling; heterocycles; metalation; organometallics; zincation; DEPROTONATIVE METALATION; REVERSE TRANSMETALATION; CHEMOSELECTIVE BASE; DIAZINES PYRIDINES; AMIDE ACTIVATION; DERIVATIVES; GENERATION; QUINOLINES; REACTIVITY; EFFICIENT;

D O I：

10.1002/chem.200801558

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A wide range of polyfunctional aryl and heteroaryl zinc reagents were efficiently prepared in THF by using (TMP)(2)Mg center dot 2LiCl (TMP = 2,2,6,6-tetramethylpiperamidyl) in the presence of ZnCl2. The possible pathways of this metalation procedure as well as possible reactive intermediates are discussed. This experimental protocol expands the tolerance of functional groups and allows an efficient zincation of sensitive heterocycles such as quinoxaline or pyrazine. The zincated arenes and heteroarenes react with various electrophiles providing the expected products in 60-95 % yield.

引用

页码：457 / 468

页数：12

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