Regio- and Chemoselective Synthesis of Fully Substituted Thiophenes

被引：65

作者：

Piller, Fabian M. ^{[1
]}

Knochel, Paul ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 02期

基金：

欧洲研究理事会;

关键词：

FUNCTIONALIZATION; MAGNESIATIONS; DERIVATIVES; METALATION; REAGENTS; ARENES; ARYL;

D O I：

10.1021/ol802513q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A full functionalization of all four positions of the thiophene ring was achieved. Starting from readily available 2,5-dichlorothiophene, successive magnesiations of the 3- and 4-positions using TMPMgCl center dot LiCl furnish, after trapping with various electrophiles, 3,4-difunctionalized dichlorothiophenes. Subsequent dechlorination and metalation or magnesium insertion into the C-Cl bond provides fully functionalized thiophenes in high yields. An application to the synthesis of a thiophene analogue of Atorvastatin (Lipitor) is reported.

引用

页码：445 / 448

页数：4

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