Polymer and metal oxide supported alkali metal naphthalenides: Application in the generation of lithium and sodium reagents

Highly coloured paramagnetic polymer supported lithium 5,5′ and sodium 6,6′ naphthalenide complexes have been prepared from the reaction of THF solutions of lithium and sodium biphenylide with polystyrene bearing -CH₂SiMe₂(C₁₀H₇) groups. Treating chloropropyl functionalised silica, alumina and titania surfaces with H₃Al · NMe₃ or H₃Ga · NMe₃ afford hydroxyl depleted surfaces. Successive treatment with lithium biphenylide, 1-(chlorodimethylsilyl)naphthalene and an alkali biphenylide affords supported alkali naphthalenide complexes which generate in high yield lithium and sodium reagents when treated with a range of organic halides, nitriles and phosphates, as found for 6,6′ and 7,7′.