Deprotonation of thiophenes using lithium magnesates

被引：45

作者：

Bayh, O

Awad, H

Mongin, F

Hoarau, C

Trécourt, F

Quéguiner, G

Marsais, F

Blanco, F

Abarca, B

Ballesteros, R

机构：

[1] Univ Rouen, Lab Chim Organ Fine & Heterocycl, IRCOF, CNRS,UMR 6014, F-76131 Mont St Aignan, France

[2] INSA, F-76131 Mont St Aignan, France

[3] Univ Valencia, Fac Farm, Dept Quim Organ, Valencia 46100, Spain

来源：

TETRAHEDRON | 2005年 / 61卷 / 20期

关键词：

D O I：

10.1016/j.tet.2005.03.024

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Thiophene was regioselectively deprotonated at C2 on treatment with 1/3 equiv of Bu3MgLi in THF at room temperature. The lithium arylmagnesate formed was either trapped with electrophiles or cross-coupled in a 'one-pot' procedure with aryl halides under palladium catalysis. 2-Chlorothiophene and 2-methoxythiophene were similarly deprotonated at C5 under the same reaction conditions. The enhancement of the reactivity of the base using TMEDA was evidenced using H-1 NMR spectroscopy. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：4779 / 4784

页数：6

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