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.