The Synthesis and Dynamic Covalent Chemistry of Amidoboronates
BN containing heterocycles can give access to different and interesting reactivity as well as functionality compared to their carbon analogues. Amidoboronates are a novel class of BN containing heterocycles readily synthesised from N-aryl iminoboronates through a reductive coupling using a single electron reductant (Dalton Trans., 2023 , 52, 9189 - 9201).
The reductive coupling yields up to 3 different amidoboronate isomers, the diastereomeric rac5 and meso5 products and the fused six-membered rac6 ring system (Chem. Eur. J., 2018 , 24 , 1200 - 12005). Amidoboronates potentially contain up to 3 types of dynamic covalent bonds including previously unknown dynamic B-N bonds. We have shown that the rac5/rac6 isomeric ratio can be influenced through variation of the para-aniline substituent and catechol sub-components through exploitation of the dynamic covalent B-N and B-O bonds (ChemPlusChem, 2022 , 87 , e20220022).
Figure from ChemPlusChem, 2022 , 87, e20220022