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2001•European Journal of Organic ChemistryRequires access

First Regioselective C-2 Lithiation of 3- and 4-Chloropyridines

Sabine Choppin, Philippe C. Gros, Yves Fort

Open publisher page 32 citations

Abstract

We have shown that the BuLi/LiDMAE reagent promotes the clean and regioselective C2 lithiation of 3- and 4-chloropyridines, while other reagents such as LDA or BuLi/TMEDA lead to classical ortho lithiation products or mixtures of regioisomers. The method was successfully applied to the preparation of various reactive 2,3- and 2,4-disubstituted pyridines.

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What this paper is about

We have shown that the BuLi/LiDMAE reagent promotes the clean and regioselective C2 lithiation of 3- and 4-chloropyridines, while other reagents such as LDA or BuLi/TMEDA lead to classical ortho lithiation products or mixtures of regioisomers. The method was successfully applied to the preparation of various reactive 2,3- and 2,4-disubstituted pyridines.

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Available abstract

We have shown that the BuLi/LiDMAE reagent promotes the clean and regioselective C2 lithiation of 3- and 4-chloropyridines, while other reagents such as LDA or BuLi/TMEDA lead to classical ortho lithiation products or mixtures of regioisomers. The method was successfully applied to the preparation of various reactive 2,3- and 2,4-disubstituted pyridines.

Key concepts: Regioselectivity, Chemistry, Reagent, Structural isomer, Combinatorial chemistry, Organic chemistry, Stereochemistry, Catalysis

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