Tetrahedron

TMSCH 2 Li–LiDMAE: a new nonnucleophilic reagent for C-2 lithiation of halopyridines

A Doudouh, PC Gros, Y Fort, C Woltermann

Index: Doudouh, Abdelatif; Gros, Philippe C.; Fort, Yves; Woltermann, Christopher Tetrahedron, 2006 , vol. 62, # 26 p. 6166 - 6171

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Citation Number: 23

Abstract

A new superbasic reagent has been discovered by combining TMSCH2Li and LiDMAE in hexane. This reagent was found highly efficient for the C-2 lithiation of sensitive chloro-and fluoropyridines. The metallation occurred chemo-and regioselectively at 0° C avoiding the nucleophilic addition or substrate degradation commonly obtained with other alkyllithiums even at lower temperatures.

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