Taming Heavier Group 14 Imine Analogues: Accessing Tin Nitrogen [Sn=N] Double Bonds and their Cycloaddition/Metathesis Chemistry

A systematic study to access stable stannaimines is reported, by combining different heteroleptic stannylenes with a range of organic azides. The reactions terphenyl-/hypersilyl-substituted yield the putative tin nitrogen double bond, but directly followed 1,2-silyl migration give SnII systems featuring bulky silylamido ligands. By contrast, transition from two σ donor ligand set mixed σ-donor/π-donor scaffold allows three new which can be handled at room temperature. reactivity profile these Sn=N bonded species crucially dependent on substituent atom. As such, Sn=NMes (Mes=2,4,6-Me3C6H2) system capable activating broad substrates under ambient conditions via 1,2-addition reactions, [2+2] and [4+2] cycloaddition reactions. Most interestingly, very rare examples main group multiple bond metathesis are also found viable.