Novel 2,6-disubstituted phenylboronic compounds – Synthesis, crystal structures, solution behaviour and reactivity

•2,6-Diformylphenylboronic acid: synthesis, characterization in solution and in solid.•Only one formyl group forms tautomeric hydroxy-oxaborole.•Formation of novel benzoxaboroles in the reaction with amines.

2,6-Diformylphenylboronic acid has been synthesized and characterized both in the solid state as well as in solution. In crystal, an unusual structural pattern has been found with the formation of intermolecular hydrogen bonds by B(OH)2 and CHO groups as well as water molecules. In solution tautomeric equilibrium with the formation of oxaborole ring by one of the formyl groups was proved on the basis of multinuclear NMR spectroscopy. The title compound reacts with secondary mono- and diamines to form various types of substituted benzoxaboroles, which have been characterized by XRD and spectroscopic methods.

Graphical abstract2,6-Diformylphenylboronic acid has been synthesized and characterized both in the solid state as well as in solution. The title compound reacts with secondary mono- and diamines to form various types of substituted benzoxaboroles, which have been characterized by XRD and spectroscopic methods.Figure optionsDownload full-size imageDownload as PowerPoint slide