Metalation of Pyridines with n BuLi− Li− Aminoalkoxide Mixed Aggregates: The Origin of Chemoselectivity

HK Khartabil, PC Gros, Y Fort…

Index: Khartabil, Hassan K.; Gros, Philippe C.; Fort, Yves; Ruiz-Lopez, Manuel F. Journal of the American Chemical Society, 2010 , vol. 132, # 7 p. 2410 - 2416

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Citation Number: 27

Abstract

The reactivity of alkyllithium− lithium− aminoalkoxide unimetallic superbases has been investigated. These systems are used for deprotonative lithiation of pyridine derivatives in apolar non-coordinating media with excellent regio-and chemoselectivity, in deep contrast with alkyllithium. With the aim of getting a better understanding of the chemistry behind these promising reagents, we have carried out a joint experimental and theoretical study of the ...