The selective lithiation-functionalisation of 3-picoline 1 remains a synthetic challenge since the potential electrophilicity of the azomethine bond towards alkyllithium reagents as well as a competitivity between acidic protons of the methyl group and those of the heteroaromatic ring must be considered. In fact, a survey of the literature revealed that major studies concern the abstraction of side-chain protons 1 while the selective lithiation of the pyridinic ring has been ...
