Less Is More: N(BOH)₂ Configuration Exhibits Higher Reactivity than the B₃NO₂ Heterocycle in Catalytic Dehydrative Amide Formation

Diboron substructures have emerged as a promising scaffold for the catalytic dehydrative amidation of carboxylic acids and amines. This Letter describes the design, synthesis, and evaluation of the first isolable N(BOH)₂ compound as an amidation catalyst. The new catalyst outperforms the previously reported B₃NO₂ heterocycle catalyst, with respect to turnover frequency, albeit the former gradually decomposes upon exposure to amines. This work opens up an avenue for designing a better catalyst for direct amidation.