The first lithiation of 4-(1H-1-pyrrolyl)pyridine has been realized. The use of BuLi-containing lithium aggregates induced the selective pyridine ring functionalization by taking advantage of the electron-donor effect of the pyrrole nucleus. Opportune substituents were introduced alpha to the pyridine nitrogen leading to new electron-enriched pyridylphosphine, bipyridine, and terpyridine ligands.
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Martineau et al. (2004) studied this question.
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