Exploring the Coupling of Pyridines with Dearomatized 4-Alkylpyridines

We describe approaches to the synthesis of dipyridylmethane scaffolds that have potential use in medicinal chemistry. The general strategy exploits the latent nucleophilicity of 4-alkylpyridines and the inherent electrophilicity of pyridines to achieve metal-free coupling. Stable dipyridyl methane scaffolds bearing quaternary pyridylic carbons, tertiary pyridylic alcohols, and pyridylic fluorines are reported.