439. A crystalline aluminium–carbon-based ambiphile capable of activation and catalytic transfer of ammonia in non-aqueous media
Despite recent achievements in the field of frustrated Lewis pairs (FLPs) for small molecule activations, the reversible activation and catalytic transformations of N–H-activated ammonia remain a challenge. Here we report on a rare combination of an aluminium Lewis acid and a carbon Lewis base. A so-called hidden FLP consisting of a phosphorus ylide featuring an aluminium fragment in the ortho position of a phenyl ring scaffold is introduced. Although the formation of the Lewis acid/base adduct is observed in the solid state, which at first glance leads to formally quenched FLP reactivity, we show that the title compound readily reacts with non-aqueous ammonia thermoneutrally and splits the N–H bond reversibly at ambient temperature. In addition, NH3 transfer reactions mediated by a main-group catalyst are presented. This proof-of-principle study is expected to initiate further activities in utilizing N–H-activated ammonia as a readily available, atom-economical nitrogen source.