Overview

One central molecule in this program is DATB, 1,3-dioxa-5-aza-2,4,6-triborinane. It is a six-membered heterocycle with no carbon atoms in the ring, yet it behaves as a remarkably practical catalyst for direct amidation from carboxylic acids and amines.

The point is not simply to make an unusual ring. The ring framework positions boron, nitrogen, and oxygen atoms so that carboxylic acids can be activated catalytically, allowing amide bonds to form with water as the main byproduct. That is the sort of chemistry we like: structurally odd, mechanistically rich, and useful enough to matter.

DATB is also thermally robust and has moved beyond a curiosity; a Pym-DATB derivative is commercially available. We are now extending this idea toward broader amidation chemistry and toward new boron-containing ring systems with functions that are still hiding in the periodic table.

What we are asking

Visual Notes

Representative Publications

1. Unique Physicochemical and Catalytic Properties Dictated by the B₃NO₂ Ring System
   Hidetoshi Noda, Makoto Furutachi, Yasuko Asada, Masakatsu Shibasaki,* and Naoya Kumagai*
   Nature Chem. 2017, 9, 571-577.
2. Direct N-Acylation of Sulfoximines with Carboxylic Acids Catalyzed by the B₃NO₂ Heterocycle
   Hidetoshi Noda, Yasuko Asada, Masakatsu Shibasaki,* and Naoya Kumagai*
   Chem. Commun. 2017, 53, 7447-7450.
3. All Non-Carbon B₃NO₂ Exotic Heterocycle: Synthesis, Dynamics, and Catalysis
   Christopher R. Opie, Hidetoshi Noda, Masakatsu Shibasaki,* and Naoya Kumagai*
   Chem. Eur. J. 2019, 25, 4648-4653.
4. Expeditious Access to the B₃NO₂ Heterocycle Enabling Modular Derivatization
   Ryosuke Tsutsumi, Nobuaki Kashiwagi, and Naoya Kumagai*
   J. Org. Chem. 2023, 88, 6247-6251.

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