Merging Boron with Nitrogen-Oxygen Bonds: A Review on BON Heterocycles

Abstract

Cyclic boronate esters play important roles in organic synthesis, pharmacology, supramolecular chemistry and materials science owing to their stability in air and versatile reactivity. Most of these compounds contain a B-O-C linkage with an alkoxy- or carboxylate group bound to the boron atom (e.g. boronate-diol esters, MIDA boronates). Boron chelates comprising a B-O-N motif (BON heterocycles) are much less explored, although first representatives of this class were prepared in the early 1960s. In recent years, there has been a growing interest in BON heterocycles as new chemotypes for drug design. The exocyclic B-O-N linkage, which is readily formed under mild conditions, shows surprising hydrolytic and thermal resistance. This allows the formation of BON heterocycles to be used as click-type reactions for the preparation of bioconjugates and functionally modified polymers. We believe that BON heterocycles are promising yet underrated organoboron derivatives. This review summarizes the scattered information about known types of BON heterocycles, including their synthesis, reactivity and structural data. Available applications of BON heterocycles in materials science and medicinal chemistry, along with their prospects, are also discussed. The bibliography contains 289 references.

Keywords: Boron heterocycles; Boronic acids; Hydroxylamines; Organoboron derivatives.