Preparation of a novel group of hybrid compounds N-benzyl aminoboronbenzylphosphonic and N,N′-ethylenedi(aminoboronbenzylphosphonic) acids

Two groups of new boronic acids containing aminophosphonate functions were synthesized and characterized by NMR spectroscopy and ESI-MS. Both groups of compounds were obtained by simple reactions of prepared in situ tris(trimethylsilyl) phosphite with a corresponding imine. The synthesized compounds may serve as a potential new class of building blocks, BNCT agents and supramolecular host molecules.

Graphical abstractThe new hybrid aminoboronphosphonic acids were synthesized in simple and convenient reactions and characterized by NMR spectroscopy and ESI mass spectrometry. The obtained compounds may be potential building blocks in Petasis and Suzuki reactions, BNTC agents and supramolecular host molecules.Figure optionsDownload full-size imageDownload as PowerPoint slideResearch highlights► A convenient synthesis of a novel class of aminophosphonates containing a boronic moiety is presented. ► Aminoboronbenzylphosphonates have been designed in order to find application as building blocks in organic synthesis, BNCT agents and supramolecular host molecules. ► NMR and ESI-MS characterization of aminoboronophosphonate compounds has been performed.