Unique Physicochemical and Catalytic Properties Dictated by the B3NO2 Ring System

Naoya Kumagai describes the unique physicochemical and catalytic properties dictated by the DATB ring system.

Amidation is one of the most used organic transformations for the synthesis of pharmaceuticals, functional polymers, and agrochemicals. However, there remains much scope for improvement of state-of-the-art amidation methodology. Although reagent-driven amidation has been well advanced to reliably access a myriad of amide-functionalized molecules, this methodology contains an inherent draw-back, namely the co-production of unwanted reagent-derived waste. The development of a catalytic alternative is an obvious solution but has witnessed slow progress and suffers from severely limited substrate generality and insufficient catalytic activity. An amidation catalyst powered by broad and general scope, as well as featuring high catalytic activity, would have the potential to be widely adopted in academia and industry.

Recently, a Japanese team led by Professor Masakatsu Shibasaki and Dr. Naoya Kumagai at the Institute of Microbial Chemistry (Tokyo, Japan) discovered a non-metallic catalyst characterized by a six-membered B3NO2 heterocyclic core coined DATB (1,3-dioxa-5-aza-2,4,6-triborinane), which proved to be a highly effective catalyst for dehydrative amidations.

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