Regio- and Chemoselective Zincation of Sensitive and Moderately Activated Aromatics and Heteroaromatics Using TMPZnCl•LiCl

被引：64

作者：

Bresser, Tomke ^{[1
]}

Mosrin, Marc ^{[1
]}

Monzon, Gabriel ^{[1
]}

Knochel, Paul ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 14期

基金：

欧洲研究理事会;

关键词：

MULTIPLE FUNCTIONALIZATION; PYRIMIDINE-DERIVATIVES; DIRECTED ZINCATION; TMP-ZINCATE; METALATION; MAGNESIATION; ARENES; ROUTE; BASE; GENERATION;

D O I：

10.1021/jo100884u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A broad range of functionalized aryl- and heteroarylzinc reagents were prepared via directed zincation of sensitive and moderately activated aromatics and heteroaromatics using TMPZnCl center dot LiCl under various reaction conditions. Diverse sensitive functional groups such as a nitro group, an aldehyde, an ester, and a nitrile are readily tolerated and are compatible with high metalation temperatures. Furthermore, the resulting zinc organometallics display an excellent reactivity toward various classes of electrophiles providing functionalized aromatics and heteroaromatics in high yields.

引用

收藏

页码：4686 / 4695

页数：10

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