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Directed lithiation of simple aromatics and heterocycles for synthesis of substituted derivatives

El-Hiti, Gamal A., Smith, Keith, Hegazy, Amany S., Alshammari, Mohammed B. and Masmali, Ali M. 2015. Directed lithiation of simple aromatics and heterocycles for synthesis of substituted derivatives. Arkivoc 2015 , pp. 19-48. 10.3998/ark.5550190.p008.744

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Abstract

Directed lithiation of substituted aromatics and heterocycles containing a directing metalating group with alkyllithium in anhydrous tetrahydrofuran or diethyl ether at low temperature provides the corresponding lithium intermediates. Reaction of the lithium reagents obtained in situ with various electrophiles gives the corresponding substituted derivatives in high yields. The process has been applied for various derivatives and has proven to be a convenient method for modification of ring systems. This brief review highlights the importance of directing metalating groups in directed lithiation of simple aromatic compounds and some common heterocycles as a tool for regioselective substitution.

Item Type: Article
Date Type: Published Online
Status: Published
Schools: Chemistry
Publisher: Michigan Publishing
ISSN: 1551-7012
Last Modified: 02 Sep 2017 06:29
URI: http://orca.cf.ac.uk/id/eprint/102291

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