Regioselective Metalations of Pyrimidines and Pyrazines by Using Frustrated Lewis Pairs of BF3OEt2 and Hindered Magnesium- and Zinc-Amide Bases

被引：59

作者：

Groll, Klaus ^{[1
]}

Manolikakes, Sophia M. ^{[1
]}

du Jourdin, Xavier Mollat ^{[1
]}

Jaric, Milica ^{[1
]}

Bredihhin, Aleksei ^{[1
]}

Karaghiosoff, Konstantin ^{[1
]}

Carell, Thomas ^{[1
]}

Knochel, Paul ^{[1
]}

机构：

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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 26期

关键词：

frustrated Lewis pairs; magnesium; metalation; N-heterocycles; zinc; CENTER-DOT-LICL; MULTIPLE FUNCTIONALIZATION; DIRECTED METALATION; SILICON PROTECTION; MEDIATED ZINCATION; ORTHO-SITES; DERIVATIVES; DIAZINES; REAGENTS; LIGANDS;

D O I：

10.1002/anie.201301694

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Born of frustration: Using the frustrated Lewis pairs TMP-metal and BF 3×OEt2 allows the regioselective metalation of pharmaceutically relevant diazines, such as pyrimidines, purines, and pyrazines. These metalations are often complementary to prior deprotonations performed without BF3×OEt2. Especially attractive is a new sequential regioselective full functionalization of the pyrazine scaffold with a bulky (TMS)2CH substituent. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：6776 / 6780

页数：5