N–H Bond Activation of Ammonia Using Intramolecular cAAC-Borane Lewis Pairs

We present the reactivity of an intramolecular cyclic (alkyl)(amino)carbene-borane Lewis adduct (1) with water and ammonia. Unlike the reaction with water, which promotes BBN ring expansion, ammonia undergoes N–H bond activation. The product is susceptible to additional deprotonation, representing a reactivity mode distinct from previously reported examples. This deprotonation reaction enabled isolation of a borane-stabilized lithium amide, an uncommon example of a linear lithium complex.