Alkyl lithium-catalyzed benzylic C-H bond addition of alkyl pyridines to α-alkenes.

Brønsted base catalyzed C-C bond formation reactions have been extensively utilized as reliable, efficient, and atom economical methods in organic synthesis. However, the electrophiles were mostly limited to polar ones such as imines, carbonyl compounds, α,β-unsaturated compounds, styrenes and conjugated dienes. The use of α-alkenes as electrophiles in the C-C bond formation reactions always needs transition metal catalysts. Herein, we reported an alkyl lithium-catalyzed benzylic C-H bond addition of alkyl pyridines to α-alkenes. The alkyl lithium catalyst displayed quite different selectivity from those of transition metal catalysts.