Alkali-metal-mediated zincation of polycyclic aromatic hydrocarbons : synthesis and structures of mono- and dizincated naphthalenes

Since the pioneering work of Schlenk nearly a century ago, alkali-metal–organic compounds (organolithium reagents, in particular) have served as frontline reagents in the battle to advance chemical synthesis. Metal–hydrogen exchange (metalation) in which a relatively inert carbon–hydrogen bond is transformed into a more labile carbon–alkali-metal bond, thus opening up a myriad of bond-forming possibilities at the carbon center, represents one of the oldest and still most important general uses of these centurial reagents.[1, 2