BORON-NITROGEN COMPOUNDS IN THE REACTION OF BORIC AND BORONIC ACIDS WITH AMINES

Abstract

The article is a review of boric or arylboronic acids reactions with aliphatic and aromatic amines. The review is for informational purposes only on the interaction of the acids in question with amines. It is shown that the data on the boric acid reaction with amines are contradictory and, at present, there is no confirmed information on obtaining a covalent bond between boron and nitrogen without the involvement of hydroxyl groups and the cyclic systems formation, for example, in the oxazaborolidines case. Literary searches have shown that the report on the anilinboronic acid production in 1963 was not developed, and there is also no data on the synthesis of those compounds. Along with this, boric acid easily forms borate salts of various configurations with amines, that is confirmed by modern methods of analysis (IR- and NMR-spectroscopy, elemental analysis). It has also been shown that boric acid is capable of forming compounds with an intramolecular donor-acceptor bond between boron and nitrogen. The theoretical calculations results and experimental data on the arylboronic acids interaction, with various aromatic ring substituents, with pyrocatechines, o-phenylenediamines, 2-hydroxybenzenetiols and o-benzenedithiols are presented. It is noted that competitive formation of anhydride-like structures is observed in all these reactions. It is shown that the interaction with pyrocatechins is the most thermodynamically advantageous. In the arylboronic acids reaction with ortho-benzenedithiols, ortho-hydroxybenzenetiols in chloroform, the corresponding oxathiaboroles and dithiaboroles were not isolated. The latter were obtained by the boron trichloride reaction with the corresponding electron donors. It is reported that there is no information on the preparation of condensation products of phenylboronic acids with aniline and benzylamine. For citation: Strokova S.V., Lenskiy M.A. Boron-nitrogen compounds in the reaction of boric and boronic acids with amines. ChemChemTech [Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol.]. 2024. V. 67. N 6. P. 6-13. DOI: 10.6060/ivkkt.20246706.6988.