Aminoalkoxide-Mediated Formation and Stabilization of Phenylpyridyllithium: Straightforward Access to Phenylpyridine Derivatives

It is shown that lithium aggregates promoted the efficient metalation of phenylpyridines and stabilization of phenylpyridyllithium. The BuLi-LiDMAE superbase prevented dimerization or nucleophilic addition encountered with t-BuLi or n-BuLi. The reported selective pyridine ring lithiation of 2-, 3-, and 4-phenylpyridine alpha to nitrogen opens a straightforward access to their derivatives.