It has been found that halogen-lithium exchange between α-substituted 2-bromo-β-methoxystyrene
derivatives and n-butyllithium generates α-substituted 2-lithio-β-methoxystyrene derivatives, which
successfully react with a range of nitriles to afford the corresponding 1,4-disubstituted
isoquinolines in reasonable yields.
benzyl anion - isoquinoline - nitrile - organolithium - styrene