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

被引：20

作者：

El-Hiti, Gamal A. ^{[1
]}

Smith, Keith ^{[2
]}

Hegazy, Amany S. ^{[2
]}

Alshammari, Mohammed B. ^{[3
]}

Masmali, Ali M. ^{[1
]}

机构：

[1] King Saud Univ, Coll Appl Med Sci, Dept Optometry, Cornea Res Chair, Riyadh 11433, Saudi Arabia

[2] Cardiff Univ, Sch Chem, Cardiff CF10 3AT, S Glam, Wales

[3] Salman bin Abdulaziz Univ, Coll Humanities & Sci, Dept Chem, Al Kharij 11942, Saudi Arabia

来源：

ARKIVOC | 2015年

关键词：

Lithium reagents; directed lithiation; lithium intermediates; electrophiles; substituted aromatics; heterocycles; synthesis; SIDE-CHAIN SUBSTITUTION; REGIOSPECIFIC ELECTROPHILIC SUBSTITUTION; ORTHO-SELECTIVE METALATION; H BOND ACTIVATION; EFFICIENT SYNTHESIS; HALOGEN-DANCE; REGIOSELECTIVE LITHIATION; ORTHO-FUNCTIONALIZATION; CONVENIENT PROCEDURE; 1ST METALATION;

D O I：

10.3998/ark.5550190.p008.744

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：19 / 47

页数：30

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