Aggregative activation in heterocyclic chemistry. Part 5.† Lithiation of pyridine and quinoline with the complex base BuLi·Me2N(CH2)2OLi (BuLi·LiDMAE)
Abstract
It is shown that the complex base BuLi·LiDMAE reacts with pyridine to give metallated species which, after trapping by electrophiles, lead to 2-substituted pyridines in good to excellent yields. The same reactions have been less successfully performed with quinoline.